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13726-69-7

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13726-69-7 Usage

Uses

boc-trans-Hydroxy-L-proline is used in the preparation of hydroxyproline derivatives. boc-trans-Hydroxy-L-proline is an intermediate in the synthesis of Fosinopril-d5 Sodium Salt (F727803), the labeled analogue of Fosinopril Sodium Salt (F727800), a phosphinic acid containing angiotensin converting enzyme (ACE) inhibitor. Antihypertensive.

Chemical Properties

White powder

Check Digit Verification of cas no

The CAS Registry Mumber 13726-69-7 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 1,3,7,2 and 6 respectively; the second part has 2 digits, 6 and 9 respectively.
Calculate Digit Verification of CAS Registry Number 13726-69:
(7*1)+(6*3)+(5*7)+(4*2)+(3*6)+(2*6)+(1*9)=107
107 % 10 = 7
So 13726-69-7 is a valid CAS Registry Number.
InChI:InChI=1/C10H17NO5/c1-10(2,3)16-9(15)11-5-6(12)4-7(11)8(13)14/h6-7,12H,4-5H2,1-3H3,(H,13,14)

13726-69-7 Well-known Company Product Price

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  • TCI America

  • (B1635)  trans-N-(tert-Butoxycarbonyl)-4-hydroxy-L-proline  >98.0%(T)

  • 13726-69-7

  • 5g

  • 540.00CNY

  • Detail
  • Alfa Aesar

  • (H27110)  N-Boc-trans-4-hydroxy-L-proline, 97%   

  • 13726-69-7

  • 1g

  • 295.0CNY

  • Detail
  • Alfa Aesar

  • (H27110)  N-Boc-trans-4-hydroxy-L-proline, 97%   

  • 13726-69-7

  • 5g

  • 573.0CNY

  • Detail
  • Alfa Aesar

  • (H27110)  N-Boc-trans-4-hydroxy-L-proline, 97%   

  • 13726-69-7

  • 25g

  • 2086.0CNY

  • Detail
  • Aldrich

  • (15544)  Boc-Hyp-OH  ≥98.0% (TLC)

  • 13726-69-7

  • 15544-5G

  • 542.88CNY

  • Detail
  • Aldrich

  • (15544)  Boc-Hyp-OH  ≥98.0% (TLC)

  • 13726-69-7

  • 15544-25G

  • 2,075.58CNY

  • Detail

13726-69-7SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 20, 2017

Revision Date: Aug 20, 2017

1.Identification

1.1 GHS Product identifier

Product name Boc-L-Hydroxyproline

1.2 Other means of identification

Product number -
Other names N-BOC-L-Hydroxyproline

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:13726-69-7 SDS

13726-69-7Synthetic route

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In water; acetone at 50℃; for 1h;100%
In tetrahydrofuran; water at 20℃; for 12h;100%
With sodium hydroxide In tetrahydrofuran; water at 20℃;100%
4N-sodium hydroxide

4N-sodium hydroxide

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-hydroxyproline
51-35-4, 913000-57-4

4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride In methanol; ethyl acetate96%
1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With water; lithium hydroxide In methanol at 20℃; for 1h;58%
With sodium hydroxide In tetrahydrofuran at 0℃; for 19h;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With water; sodium hydroxide In methanol for 4h;
Stage #2: With citric acid In methanol; water pH=3; Product distribution / selectivity;
Stage #1: 1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate With methanol; water; lithium hydroxide at 20℃; Inert atmosphere;
Stage #2: With hydrogenchloride In water; acetonitrile for 0.166667h; Cooling with ice bath; Inert atmosphere;
tert-butyldicarbonate
34619-03-9

tert-butyldicarbonate

4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydrogencarbonate In 1,4-dioxane; water at 20℃;97%
With sodium hydroxide In water; tert-butyl alcohol at 20℃; for 16h;89%
With sodium hydrogencarbonate In water
4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In water95%
(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate
184046-78-4

(2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,3S)-1-tert-butyl-2-methyl 3-hydroxypyrrolidine-1,2-dicarboxylate With water; sodium hydroxide In methanol for 6h;
Stage #2: With citric acid In methanol; water pH=3;
potassium hydrogen sulphate

potassium hydrogen sulphate

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

4-hydroxyproline
51-35-4, 913000-57-4

4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
In sodium hydroxide; hexane; water; tert-butyl alcohol
water
7732-18-5

water

4-hydroxyproline
51-35-4, 913000-57-4

4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With sodium hydroxide In 1,4-dioxane
dipercarbonate de O,O-t-butyle
3236-56-4

dipercarbonate de O,O-t-butyle

4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With hydrogenchloride; sodium hydroxide; ammonium chloride In tetrahydrofuran; water
(2R)-1-benzyloxy-2-hydroxy-pent-4-yne
115352-39-1, 124662-61-9, 110339-26-9

(2R)-1-benzyloxy-2-hydroxy-pent-4-yne

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogen / Pd/CaCO3 / ethyl acetate
2: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C
3: hydrazine / ethanol / 6 h / Heating
4: Et3N / CH2Cl2
5: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
6: Et3N / CH2Cl2
7: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
8: K2CO3 / methanol
View Scheme
N-tert-butoxycarbonyl-4-oxo-L-proline
84348-37-8

N-tert-butoxycarbonyl-4-oxo-L-proline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 90 percent / sodium borohydride / methanol / 3.5 h / 0 °C
2: 62 percent / aq. NaOH / diethyl ether / 24 h
3: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
4: trifluoroacetic acid / 0.5 h
5: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
6: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
N-tert-butoxycarbonyl-L-cis-4-hydroxyproline
87691-27-8

N-tert-butoxycarbonyl-L-cis-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 62 percent / aq. NaOH / diethyl ether / 24 h
2: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
3: trifluoroacetic acid / 0.5 h
4: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
5: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
(2S,4R)-<4-2H1>-proline
153790-69-3

(2S,4R)-<4-2H1>-proline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
2: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
C10H16(2)HNO4

C10H16(2)HNO4

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: trifluoroacetic acid / 0.5 h
2: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
3: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
N-Boc-D-cis-4-(p-toluenesulfonyloxy)proline
153790-67-1

N-Boc-D-cis-4-(p-toluenesulfonyloxy)proline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 36 percent / lithium triethylborodeuteride / tetrahydrofuran / 24 h / Heating
2: trifluoroacetic acid / 0.5 h
3: TES buffer, iron(II)ammonium sulphate, 2-oxoglutarate, proline 4-hydroxylase / 4 h / 26 °C / incubation
4: 85 percent / aq. NaOH / 2-methyl-propan-2-ol / 18 h
View Scheme
(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid
90600-20-7

(2S)-2-[(tert-butoxycarbonyl)amino]pent-4-enoic acid

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: 73 percent / N-bromosuccinimide / tetrahydrofuran / 0.33 h / 0 °C
2: 100 percent / K2CO3 / 0.5 h / 0 °C
3: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
4: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
5: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
6: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
7: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(2S,4S)-2-(tert-butoxycarbonyl)amino-4-bromomethyl-γ-butyrolactone
104241-30-7

(2S,4S)-2-(tert-butoxycarbonyl)amino-4-bromomethyl-γ-butyrolactone

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 100 percent / K2CO3 / 0.5 h / 0 °C
2: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
3: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
4: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
5: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
6: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(2S,4R)-2-tert-butoxycarbonylamino-4-hydroxymethyl-4-butanolide
104241-32-9

(2S,4R)-2-tert-butoxycarbonylamino-4-hydroxymethyl-4-butanolide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
2: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
3: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
4: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(2S,4R)-2-(tert-butoxycarbonyl)amino-4-formyl-γ-butyrolactone
106391-74-6

(2S,4R)-2-(tert-butoxycarbonyl)amino-4-formyl-γ-butyrolactone

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
2: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
3: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(2S,4S)-2-(tert-butoxycarbonyl)amino-3,4-epoxypentanoic acid methyl ester
104241-31-8

(2S,4S)-2-(tert-butoxycarbonyl)amino-3,4-epoxypentanoic acid methyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: 1) 0.5 N NaOH, 2) dl-10-camphorsulfonic acid / 1) THF, 0 deg C, 14 h, 2) CH2Cl2, RT, 20 h
2: 1) (COCl)2, DMSO, 2) NEt3 / 1a) CH2Cl2, -78 deg C, 15 min, 1b) -45 deg C, 1 h, 2a) -45 deg C, 20 min, 2b) 0 deg C, 15 min
3: 78 percent / p-TsOH*H2O / 14 h / Ambient temperature
4: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
5: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(4R)-N-(tert-butoxycarbonyl)-4-hydroxy-5-methoxyproline methyl ester

(4R)-N-(tert-butoxycarbonyl)-4-hydroxy-5-methoxyproline methyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 1) 60percent HOAc, 2) NaBH3CN, HOAc / 1) RT, 3 d, 2) EtOH, RT, 1 h
2: 0.5 N NaOH / tetrahydrofuran / 19 h / 0 °C
View Scheme
(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
121795-00-4

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium carbonate In methanol
(R)-1-benzyloxypent-4-en-2-ol
58931-16-1, 88981-35-5, 110339-28-1

(R)-1-benzyloxypent-4-en-2-ol

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: di-isopropyl azodicarboxylate, Ph3P / tetrahydrofuran / 12 h / -20 °C
2: hydrazine / ethanol / 6 h / Heating
3: Et3N / CH2Cl2
4: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
5: Et3N / CH2Cl2
6: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
7: K2CO3 / methanol
View Scheme
(S)-1-(benzyloxy)pent-4-en-2-amine
121794-95-4

(S)-1-(benzyloxy)pent-4-en-2-amine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: Et3N / CH2Cl2
2: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
3: Et3N / CH2Cl2
4: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
5: K2CO3 / methanol
View Scheme
N-((S)-1-Benzyloxymethyl-but-3-enyl)-benzamide
121794-96-5

N-((S)-1-Benzyloxymethyl-but-3-enyl)-benzamide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
2: Et3N / CH2Cl2
3: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
4: K2CO3 / methanol
View Scheme
O-benzyl-(2S,4R)-4-benzoyloxyprolinol
121794-97-6

O-benzyl-(2S,4R)-4-benzoyloxyprolinol

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / CH2Cl2
2: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
3: K2CO3 / methanol
View Scheme
2-((S)-1-Benzyloxymethyl-but-3-enyl)-isoindole-1,3-dione
121794-94-3

2-((S)-1-Benzyloxymethyl-but-3-enyl)-isoindole-1,3-dione

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: hydrazine / ethanol / 6 h / Heating
2: Et3N / CH2Cl2
3: 78 percent / I2 / tetrahydrofuran; H2O / 6 h / 20 °C
4: Et3N / CH2Cl2
5: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
6: K2CO3 / methanol
View Scheme
(2S,4R)-4-Benzoyloxy-2-benzyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester
121794-98-7

(2S,4R)-4-Benzoyloxy-2-benzyloxymethyl-pyrrolidine-1-carboxylic acid tert-butyl ester

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: RuCl3*H2O, NaIO4, / CCl4; acetonitrile; H2O / 1 h / Ambient temperature
2: K2CO3 / methanol
View Scheme
4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

BocON

BocON

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With triethylamine
N-(tert-butyloxycarbonyl) azide
1070-19-5

N-(tert-butyloxycarbonyl) azide

4R-4-hydroxyproline
51-35-4

4R-4-hydroxyproline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Conditions
ConditionsYield
In methanol100%
In methanol; diethyl ether100%
In tetrahydrofuran96%
benzyl bromide
100-39-0

benzyl bromide

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
40350-83-2, 54631-82-2, 54631-81-1

(2S,4R)-4-(benzyloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 6h; Inert atmosphere; chemoselective reaction;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; mineral oil at 0℃; for 1h; Inert atmosphere;
Stage #2: benzyl bromide In tetrahydrofuran; mineral oil Inert atmosphere;
90%
With sodium hydride; 18-crown-6 ether 1.) THF, 0 degC, 1 h, and 30 min, RT, 2.) 0 degC, 1 h and 50 degC, overnight, THF; Yield given. Multistep reaction;
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

N-methyl-N-(phenylmethyl)-L-phenylalaninamide hydrochloride
126090-32-2

N-methyl-N-(phenylmethyl)-L-phenylalaninamide hydrochloride

Boc-(2S,4R)Hyp-Phe-NMeBzl
131949-55-8

Boc-(2S,4R)Hyp-Phe-NMeBzl

Conditions
ConditionsYield
With benzotriazol-1-ol In dichloromethane Ambient temperature;100%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate
109384-24-9

tert-butyl (2S,4R)-2-(aminocarbonyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 6h;
Stage #2: With ammonium hydroxide In acetonitrile at 0 - 20℃; for 1.5h;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -15℃; for 0.166667h; Inert atmosphere;
Stage #2: With ammonia In tetrahydrofuran; water at -15 - 5℃; for 2h;
86%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at -10℃; for 1h;
Stage #2: With ammonia In tetrahydrofuran; water at -5 - 20℃; for 2h;
59%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃;
Stage #2: With ammonium hydroxide In acetonitrile
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane; N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: With ammonium chloride In dichloromethane; N,N-dimethyl-formamide at 20℃; for 2h;
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

diazomethyl-trimethyl-silane
18107-18-1

diazomethyl-trimethyl-silane

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate
74844-91-0

1-tert-butyl 2-methyl (2S,4R)-4-hydroxy-1,2-pyrrolidinedicarboxylate

Conditions
ConditionsYield
In methanol at 0℃; for 1h;100%
In methanol; hexane; benzene at 20℃; for 1h;
In tetrahydrofuran; methanol; toluene at -78 - 23℃; for 0.166667h; Inert atmosphere;
7-chloro-5-pyridin-2-ylthieno[3,2-b]pyridine
884538-46-9

7-chloro-5-pyridin-2-ylthieno[3,2-b]pyridine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-(5-(pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)pyrrolidine-2-carboxylic acid
884538-47-0

(2S,4R)-1-(tert-butoxycarbonyl)-4-(5-(pyridin-2-yl)thieno[3,2-b]pyridin-7-yloxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 70h;100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide for 2h;
Stage #2: 7-chloro-5-pyridin-2-ylthieno[3,2-b]pyridine In dimethyl sulfoxide at 30℃; for 90h;
Stage #3: With hydrogenchloride In water pH=4.5;
57%
1-chloro-6-methoxyisoquinoline
132997-77-4

1-chloro-6-methoxyisoquinoline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-((6-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid
630421-67-9

(2S,4R)-1-(tert-butoxycarbonyl)-4-((6-methoxyisoquinolin-1-yl)oxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 2h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 20℃; for 0.5h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
99%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 10 - 20℃; for 0.5h;
Stage #2: 1-chloro-6-methoxyisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
99%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

allyl bromide
106-95-6

allyl bromide

(2S,4R)-4-(but-3-en-1-yloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid
93962-39-1

(2S,4R)-4-(but-3-en-1-yloxy)-1-(tert-butoxycarbonyl)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: allyl bromide In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 6h; Inert atmosphere; chemoselective reaction;
100%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; allyl bromide With sodium hydride In N,N-dimethyl-formamide at -25 - 20℃;
Stage #2: With sodium hydroxide In methanol at 0 - 20℃;
67%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydroxide In tetrahydrofuran; mineral oil at 20℃; for 1h; Inert atmosphere;
Stage #2: allyl bromide With 18-crown-6 ether In tetrahydrofuran; mineral oil at 20 - 50℃;
1,3-dichloroisoquinoline
7742-73-6

1,3-dichloroisoquinoline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

C19H21ClN2O5
630425-54-6

C19H21ClN2O5

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In DMF (N,N-dimethyl-formamide) at 0℃; for 0.5h;
Stage #2: 1,3-dichloroisoquinoline In DMF (N,N-dimethyl-formamide) at 20℃; for 12h;
99.8%
1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine
1448189-30-7

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

tert‐butyl (2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidine‐1‐carboxylate
1448191-54-5

tert‐butyl (2S,4R)‐4‐hydroxy‐2‐({[4‐(4‐methyl‐1,3‐thiazol‐5‐yl)phenyl]methyl}carbamoyl)pyrrolidine‐1‐carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With triethylamine In N,N-dimethyl-formamide at 0℃; for 0.0833333h;
Stage #2: 1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine In N,N-dimethyl-formamide at 20℃;
99.49%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide for 15h;98%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 15h;98%
1-ethyl-cyclopropane-sulfonic acid [1(R)-amino-2(S)-vinyl-cyclopropanecarbonyl]-amide hydrochloride
853269-47-3

1-ethyl-cyclopropane-sulfonic acid [1(R)-amino-2(S)-vinyl-cyclopropanecarbonyl]-amide hydrochloride

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

2(S)-[1(R)-(1-ethyl-cyclopropanesulfonylaminocarbonyl)-2(S)-vinyl-cyclopropylcarbamoyl]-4(R)-hydroxy-N-Boc-pyrrolidone
853269-48-4

2(S)-[1(R)-(1-ethyl-cyclopropanesulfonylaminocarbonyl)-2(S)-vinyl-cyclopropylcarbamoyl]-4(R)-hydroxy-N-Boc-pyrrolidone

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate In dichloromethane at 20℃; for 1h;99%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1-bromo-3-phenylprop-2-yne
1794-48-5

1-bromo-3-phenylprop-2-yne

C19H23NO5
872496-90-7

C19H23NO5

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride at 20℃; for 1h;
Stage #2: 1-bromo-3-phenylprop-2-yne for 16h; Heating / reflux;
99%
methanol
67-56-1

methanol

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

L-4-hydroxyproline methyl ester hydrochloride
40216-83-9

L-4-hydroxyproline methyl ester hydrochloride

Conditions
ConditionsYield
With hydrogenchloride at 20℃; for 12h;99%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1-bromomethyl-4-bromobenzene
589-15-1

1-bromomethyl-4-bromobenzene

C17H22BrNO5
1374041-49-2

C17H22BrNO5

Conditions
ConditionsYield
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 0 - 20℃;99%
With caesium carbonate In 1-methyl-pyrrolidin-2-one at 0 - 20℃;99%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

benzyl-methyl-amine
103-67-3

benzyl-methyl-amine

(2S,4R)-2-(Benzyl-methyl-carbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester
330583-66-9

(2S,4R)-2-(Benzyl-methyl-carbamoyl)-4-hydroxy-pyrrolidine-1-carboxylic acid tert-butyl ester

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃; for 6h;98%
4-chloro-7-methoxy-2-phenylquinoline
189816-05-5

4-chloro-7-methoxy-2-phenylquinoline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-2-carboxylic acid
259214-37-4

(2S,4R)-1-(tert-butoxycarbonyl)-4-(7-methoxy-2-phenylquinolin-4-yloxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 25h;
98%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 25h;
98%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0℃; for 1.5h;
Stage #2: 4-chloro-7-methoxy-2-phenylquinoline In dimethyl sulfoxide for 24h;
Stage #3: pH=4.6; Acidic aqueous solution;
98%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

tert-butyldimethylsilyl chloride
18162-48-6

tert-butyldimethylsilyl chloride

methyl iodide
74-88-4

methyl iodide

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
1374161-77-9

(2S,4R)-4-(tert-butyldimethylsilanyloxy)-2-methylpyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid; methyl iodide With potassium carbonate In N,N-dimethyl-formamide at 0 - 20℃; for 5h;
Stage #2: tert-butyldimethylsilyl chloride With 1H-imidazole In N,N-dimethyl-formamide at 0 - 20℃; for 2h;
98%
1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine
1448189-30-7

1-[4-(4-methyl-1,3-thiazol-5-yl)phenyl]methaneamine

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-tert-butyl 4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carboxylate

(2S,4R)-tert-butyl 4-hydroxy-2-((4-(4-methylthiazol-5-yl)benzyl)carbamoyl)pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide for 0.0833333h;
Stage #2: [4-(4-methyl-1,3-thiazol-5-yl)phenyl]methanamine In N,N-dimethyl-formamide for 15h;
98%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate
87250-97-3, 113775-22-7

2’-methyl-2’-propanyl (1S,4S)-3-oxo-2-oxa-5-azabicyclo[2.2.1]heptane-5-carboxylate

Conditions
ConditionsYield
With di-isopropyl azodicarboxylate; triphenylphosphine In tetrahydrofuran at 20℃; for 20h; Mitsunobu reaction;97%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran at 20℃; for 20h; Mitsunobu Displacement; Inert atmosphere;87%
With triphenylphosphine; diethylazodicarboxylate In tetrahydrofuran82%
(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate
746657-36-3

(1R,2S)-ethyl 1-amino-2-vinylcyclopropanecarboxylate

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate
862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;97%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;96%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;96%
(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester tosylate salt
1159609-95-6

(1R,2S)-1-amino-2-vinylcyclopropanecarboxylic acid ethyl ester tosylate salt

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate
862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; for 4.5h;97%
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃;89%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

tert-butylchlorodiphenylsilane
58479-61-1

tert-butylchlorodiphenylsilane

trans-4-tert-butyldiphenylsiloxy-N-Boc-L-proline carboxylic acid
1357471-22-7

trans-4-tert-butyldiphenylsiloxy-N-Boc-L-proline carboxylic acid

Conditions
ConditionsYield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In acetonitrile at 50℃; for 4h; Reflux;97%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate
61478-26-0

tert-butyl (2S,4R)-4-hydroxy-2-hydroxymethyl-pyrrolidine-1-carboxylate

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.25h;
Stage #2: With methanol In tetrahydrofuran at 20℃; for 62h;
96%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With borane-THF In tetrahydrofuran at 0 - 20℃; for 4.25h;
Stage #2: With methanol In tetrahydrofuran at 0 - 20℃; for 62h;
96%
With borane-THF at 0℃; for 1h; Inert atmosphere;96%
1-chloroisoquinoline
19493-44-8

1-chloroisoquinoline

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

4-(isoquinoline-1-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester
630421-77-1

4-(isoquinoline-1-yloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester

Conditions
ConditionsYield
Stage #1: 1-chloroisoquinoline; (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 0 - 20℃; for 25.7167h;
Stage #2:
Stage #3: With hydrogenchloride In water
96%
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With potassium tert-butylate In dimethyl sulfoxide at 10 - 20℃; for 0.5h;
Stage #2: 1-chloroisoquinoline In dimethyl sulfoxide at 20℃; for 12h;
Stage #3: With citric acid In water; dimethyl sulfoxide at 0℃; Product distribution / selectivity;
92%
ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride

ethyl (1R,2S)-1-amino-2-vinylcyclopropanecarboxylate hydrochloride

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate
862119-82-2

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine; HATU In N,N-dimethyl-formamide at 0 - 20℃; Product distribution / selectivity;96%
With 4-methyl-morpholine; HATU In dichloromethane at 20℃; for 18h;94%
With 4-methyl-morpholine; HATU In dichloromethane at 20℃; for 18h;94%
(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

1-iodo-propane
107-08-4

1-iodo-propane

(2S,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidine-2-carboxylic acid
146129-07-9

(2S,4R)-1-(tert-butoxycarbonyl)-4-propoxypyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: 1-iodo-propane In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 24h; Inert atmosphere; chemoselective reaction;
96%
1-(bromomethyl)-4-vinylbenzene
13368-25-7

1-(bromomethyl)-4-vinylbenzene

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid
13726-69-7

(2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-((4-vinylbenzyl)oxy)pyrrolidine-2-carboxylic acid

(2S,4R)-1-(tert-butoxycarbonyl)-4-((4-vinylbenzyl)oxy)pyrrolidine-2-carboxylic acid

Conditions
ConditionsYield
Stage #1: (2S,4R)-4-hydroxy-1-[(2-methylpropan-2-yl)oxycarbonyl]pyrrolidine-2-carboxylic acid With sodium hydride In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 0℃; Inert atmosphere;
Stage #2: 1-(bromomethyl)-4-vinylbenzene In tetrahydrofuran; dimethyl sulfoxide; mineral oil at -20 - 25℃; for 24h; Inert atmosphere; chemoselective reaction;
96%

13726-69-7Relevant articles and documents

An Unconventional Redox Cross Claisen Condensation-Aromatization of 4-Hydroxyprolines with Ketones

Tang, Mi,Sun, Rengwei,Li, Hao,Yu, Xinhong,Wang, Wei

, p. 8419 - 8425 (2017)

Reaction of α-amino acids, particularly prolines and their derivatives with carbonyl compounds via decarboxylative redox process, is a viable strategy for synthesis of structurally diverse nitrogen centered heterocyclics. In these processes, the decarboxylation is the essential driving force for the processes. The realization of the redox process without decarboxylation may offer an opportunity to explore new reactions. Herein, we report the discovery of an unprecedented redox Claisen-type condensation aromatization cascade reaction of 4-substituted 4-hydroxyproline and its esters with unreactive ketones. We found that the use of propionic acid as a catalyst and a co-solvent can change the reaction course. The commonly observed redox decarboxylation and aldol condensation reactions are significantly minimized. Moreover, unreactive ketones can effectively participate in the Claisen condensation reaction. The new reactivity enables a redox cyclization via an unconventional Claisen-type condensation reaction of in situ formed enamine intermediates from ketone precursors with 4-substituted 4-hydroxyproline and its esters as electrophilic acylation partners. Under the reaction conditions, the cascade process proceeds highly regio- and stereoselectively to afford highly synthetically and biologically valued cis-2,3-dihydro-1H-pyrrolizin-1-ones with a broad substrate scope in efficient 'one-pot' operation, whereas such structures generally require multiple steps.

β-L-Arabinofuranosylation Conducted by 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl Trichloroacetimidate

Li, Hong-Zhan,Ding, Jie,Cheng, Chun-Ru,Chen, Yue,Liang, Xing-Yong

, p. 1 - 7 (2018)

We describe a β-L-arabinofuranosylation method by employing the 5-O-(2-pyridinecarbonyl)-L-arabinofuranosyl trichloroacetimidate 10 as a donor. This approach allows a wide range of acceptor substrates, especially amino acid acceptors, to be used. Stereoselective synthesis of β-(1,4)-L-arabinofuranosyl-(2S, 4R)-4-hydroxy-L-proline (β-L-Araf-L-Hyp4) and its dimer is achieved readily by this method. Both the stereoselectivities and yields of the reactions are excellent. To demonstrate the utility of this methodology, the preparation of a trisaccharide in a one-pot manner was carried out.

Chemical Probes Unravel an Antimicrobial Defense Response Triggered by Binding of the Human Opioid Dynorphin to a Bacterial Sensor Kinase

Wright, Megan H.,Fetzer, Christian,Sieber, Stephan A.

, p. 6152 - 6159 (2017)

Host-microbe communication via small molecule signals is important for both symbiotic and pathogenic relationships, but is often poorly understood at the molecular level. Under conditions of host stress, levels of the human opioid peptide dynorphin are elevated, triggering virulence in the opportunistic pathogenic bacterium Pseudomonas aeruginosa via an unknown pathway. Here we apply a multilayered chemical biology strategy to unravel the mode of action of this putative interkingdom signal. We designed and applied dynorphin-inspired photoaffinity probes to reveal the protein targets of the peptide in live bacteria via chemical proteomics. ParS, a largely uncharacterized membrane sensor of a two-component system, was identified as the most promising hit. Subsequent full proteome studies revealed that dynorphin(1-13) induces an antimicrobial peptide-like response in Pseudomonas, with specific upregulation of membrane defense mechanisms. No such response was observed in a parS mutant, which was more susceptible to dynorphin-induced toxicity. Thus, P. aeruginosa exploits the ParS sensing machinery to defend itself against the host in response to dynorphin as a signal. This study highlights interkingdom communication as a potential essential strategy not only for induction of P. aeruginosa virulence but also for maintaining viability in the hostile environment of the host.

Synthesis and DNA binding property of a novel peptide nucleic acid that contains cis-4-adeninyl-L-prolinol unit

Shigeyasu, Masanori,Kuwahara, Masayasu,Sisido, Masahiko,Ishikawa, Teruhiko

, p. 634 - 635 (2001)

A novel oxy-peptide nucleic acid that contains a cis-4-adeninyl-L-prolinol unit in the main chain (PPNA) was synthesized. The peptide nucleic acid with nine adenine units [PPNA(A9)] hybridized with the complementary DNA (T9). The hybrid showed a very sharp melting curve with Tm = 34 °C.

The development of a new class of inhibitors for betaine-homocysteine S-methyltransferase

Pi?ha, Jan,Vaňek, Václav,Budě??sińsky, Milo?,Mlad?ková, Jana,Garrow, Timothy A.,Ji??acek, Ji??i

, p. 256 - 275 (2013)

Betaine-homocysteine S-methyltransferase (BHMT) is an important zinc-dependent methyltransferase that uses betaine as the methyl donor for the remethylation of homocysteine to form methionine. In the liver, BHMT performs to half of the homocysteine remethylation. In this study, we systematically investigated the tolerance of the enzyme for modifications at the "homocysteine" part of the previously reported potent inhibitor (R,S)-5-(3-amino-3-carboxy-propylsulfanyl)-pentanoic acid (1). In the new compounds, which are S-alkylated homocysteine derivatives, we replaced the carboxylic group in the "homocysteine" part of inhibitor 1 with different isosteric moieties (tetrazole and oxadiazolone); we suppressed the carboxylic negative charge by amidations; we enhanced acidity by replacing the carboxylate with phosphonic or phosphinic acids; and we introduced pyrrolidine steric constraints. Some of these compounds display high affinity toward human BHMT and may be useful for further pharmacological studies of this enzyme. Although none of the new compounds were more potent inhibitors than the reference inhibitor 1, this study helped to completely defi ne the structural requirements of the active site of BHMT and revealed the remarkable selectivity of the enzyme for homocysteine.

Locked conformations for proline pyrrolidine ring: Synthesis and conformational analysis of cis- and trans-4-tert-butylprolines

Koskinen, Ari M. P.,Helaja, Juho,Kumpulainen, Esa T. T.,Koivisto, Jari,Mansikkamaeki, Heidi,Rissanen, Kari

, p. 6447 - 6453 (2005)

The motional restrictions of the proline pyrrolidine ring allow this secondary amine amino acid to act as a turn inducer in many peptides and proteins. The pyrrolidine ring is known to exhibit two predominant pucker modes (i.e., C-4 (Cγ) exo and endo envelope conformers whose ratio can be controlled by proper substituents in the ring). In nature, the exo puckered 4(R)-hydroxy-L-proline plays a crucial role as a building block in collagen and collagen-like structures. It has been previously concluded that the electronegativity of the 4-cis-substituent increases the endo puckering while the electronegativity of the 4-trans-substituent favors the exo puckering. Here, we have introduced a sterically demanding tert-butyl group at C-4 in trans- and cis-configurations. In the case of trans-substitution, the induced puckering effect on the pyrrolidine ring was studied with X-ray crystallography and 1H NMR spectral simulations. Both cis- and trans-4-tert-butyl groups strongly favor pseudoequatorial orientation, thereby causing opposite puckering effects for the pyrrolidine ring, cis-exo and trans-endo for L-prolines, in contrast to the effects observed in the case of electronegative C-4 substituents. The syntheses and structural analysis are presented for the conformationally constrained 4-tert-butylprolines. The prolines were synthesized from 4-hydroxy-L-proline, substitution with t-BuCuSPhLi being the key transformation. This reaction gave N-Boc-trans-4-tert-butyl-L-proline tert-butyl ester in 94% ee and 57% de. Enantioselectivity was increased to 99.2% ee by crystallization of N-Boc-trans-4-tert-butyl-L-proline in the final step of the synthesis.

Design and synthesis of fluorinated peptides for analysis of fluorous effects on the interconversion of polyproline helices

Horng, Jia-Cherng,Hsu, Kuang-Cheng,Li, Meng-Che,Lin, Chih-Wei,Lin, Tse-Hsueh,Liu, Ying-Jie,Wang, Sheng-Kai

, (2021/11/30)

The unique interaction between fluorine atoms has been exploited to alter protein structures and to develop synthetic and analytical applications. To expand such fluorous interaction for novel applications, polyproline peptides represent an excellent molecular nanoscaffold for controlling the presentation of perfluoroalkyl groups on their unique secondary structure. We develop approaches to synthesis fluorinated peptides to systematically investigate how the number, location and types of the fluorous groups on polyproline affect the conformation by monitoring the transition between the two major polyproline structures PPI and PPII. This work provides valuable information on how fluorous interaction affects the peptide structure and also benefits the design of functional fluorous molecules.

Method for synthesizing tert-2-(3- (2S)-4- butyl)-1- ester of n-oxo-isothiazole alkyloxycarbonylpyrrolidinecarboxylic acid (by machine translation)

-

Paragraph 0038-0040; 0053-0055; 0066-0068, (2020/02/14)

The technical scheme of the present (2S) - 4 - invention is that the following) - 1 - technical scheme of the present invention, is that the compound is obtained. by the continuous production of the: compound having L - the following beneficial, effects: the Boc compound is obtained II, from the following technical scheme III, No.No. STR3, No.No. IV; The technical proposal of the present invention is the following technical proposal: II No.No. STR3 III. No., No. The following technical II, proposal III Boc - L - of the present, N - Boc - 4 - IV invention is the following (2S) - 4 -) - 1 - technical proposal: No.No. STR8. No. II No.No. :(1) STR8 III, No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2, No.No.No. STR8No.No.No.No. .(2) STR8No., No.No.No.. STR8No., No.No.No., STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR8No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR8No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. STR2No.No.No. STR7No.No.No.No. ST (by machine translation)

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