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33125-05-2

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33125-05-2 Usage

Chemical Properties

White powder

Uses

It is a reagent of choice for assignment of absolute configuration of chiral primary amines by 1H NMR, giving better results than Mosher's acid ((R)-(+)-?-Methoxy-?-(trifluoromethyl)-phenyl-acetic acid. αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is D-(+)-2-Phenylglycine with Boc protecting group. (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]-benzeneacetic Acid is used as part of a catalyst combination to catalyze regioselective [4 + 2] cycloadditions of β-substituted cyclic enones and polyconjugated malononitriles. It can also be used to catalyze stereoselective preparation of polyfunctional nitrocyclohexene carboxaldehydes.

Check Digit Verification of cas no

The CAS Registry Mumber 33125-05-2 includes 8 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 5 digits, 3,3,1,2 and 5 respectively; the second part has 2 digits, 0 and 5 respectively.
Calculate Digit Verification of CAS Registry Number 33125-05:
(7*3)+(6*3)+(5*1)+(4*2)+(3*5)+(2*0)+(1*5)=72
72 % 10 = 2
So 33125-05-2 is a valid CAS Registry Number.
InChI:InChI=1/C13H17NO4/c1-13(2,3)18-12(17)14(9-11(15)16)10-7-5-4-6-8-10/h46-1-2-7(5-10)8(11)3-6/h1-3,5,11H

33125-05-2 Well-known Company Product Price

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  • (Code)Product description
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  • TCI America

  • (B3230)  N-(tert-Butoxycarbonyl)-D-2-phenylglycine  >98.0%(T)

  • 33125-05-2

  • 1g

  • 190.00CNY

  • Detail
  • TCI America

  • (B3230)  N-(tert-Butoxycarbonyl)-D-2-phenylglycine  >98.0%(T)

  • 33125-05-2

  • 5g

  • 650.00CNY

  • Detail
  • Alfa Aesar

  • (L18540)  N-Boc-D-phenylglycine, 99%   

  • 33125-05-2

  • 1g

  • 299.0CNY

  • Detail
  • Alfa Aesar

  • (L18540)  N-Boc-D-phenylglycine, 99%   

  • 33125-05-2

  • 5g

  • 1073.0CNY

  • Detail
  • Aldrich

  • (15487)  Boc-D-Phg-OH  ≥99.0% (TLC)

  • 33125-05-2

  • 15487-1G

  • 286.65CNY

  • Detail
  • Aldrich

  • (15487)  Boc-D-Phg-OH  ≥99.0% (TLC)

  • 33125-05-2

  • 15487-5G

  • 1,021.41CNY

  • Detail

33125-05-2SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name (2R)-2-[(2-methylpropan-2-yl)oxycarbonylamino]-2-phenylacetic acid

1.2 Other means of identification

Product number -
Other names N-Boc-D-2-phenylglycine

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:33125-05-2 SDS

33125-05-2Synthetic route

di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

(R)-phenylglycine
875-74-1

(R)-phenylglycine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With sodium hydroxide In tert-butyl alcohol at 20℃; for 1h; Inert atmosphere;100%
With potassium hydrogencarbonate In tetrahydrofuran; water for 18h;99%
With sodium hydroxide96%
(R)-phenylglycine
875-74-1

(R)-phenylglycine

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile
58632-95-4

2-(tert-Butoxycarbonyloxyimino)-2-phenylacetonitrile

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With triethylamine In 1,4-dioxane; water for 18h;94%
(R)-phenylglycine
875-74-1

(R)-phenylglycine

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

tert-butyl (2,4-dioxo-3-azaspiro[5,5]undecan-3-yl) carbonate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With sodium carbonate In 1,4-dioxane; water at 25℃; for 12h;89%
tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate
956101-46-5

tert-butyl [(1S)-1-phenylprop-2-en-1-yl]imidocarbonate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile85%
(R)-phenylglycine
875-74-1

(R)-phenylglycine

1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate
50739-44-1

1-(t-butoxycarbonyl)-1,2,4-triazolo<4,3-a>pyridinium-3-olate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With sodium hydroxide In acetone for 2h; Ambient temperature;84%
2-(tert-butoxycarbonylamino)-2-phenylacetic acid
2900-27-8, 3601-66-9, 14675-97-9, 33125-05-2

2-(tert-butoxycarbonylamino)-2-phenylacetic acid

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
82%
(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol
125414-45-1

(2R,3R)-3-<(tert-butoxycarbonyl)amino>-3-phenyl-1,2-propanediol

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate; sodium carbonate In tetrachloromethane; water; acetonitrile for 2h; Ambient temperature;79%
(R)-N-(tert-butoxycarbonyl)phenylglycinol
67341-01-9, 117049-14-6, 138457-46-2, 102089-74-7

(R)-N-(tert-butoxycarbonyl)phenylglycinol

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile at 0 - 20℃; for 1h;77%
With dipyridinium dichromate In N,N-dimethyl-formamide Ambient temperature;
With dipyridinium dichromate In N,N-dimethyl-formamide for 6h; Ambient temperature;
C16H17F6NO4

C16H17F6NO4

A

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

B

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid
2900-27-8

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

Conditions
ConditionsYield
With C28H30N3O2(1+)*Br(1-); sodium hydroxide In chloroform at 0℃; for 24h;A n/a
B 35%
carbon dioxide
124-38-9

carbon dioxide

N-(triisopropylsilyl)-N-(tert-butyloxycarbonyl)benzylamine
186375-61-1

N-(triisopropylsilyl)-N-(tert-butyloxycarbonyl)benzylamine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Stage #1: N-(triisopropylsilyl)-N-(tert-butyloxycarbonyl)benzylamine With sec.-butyllithium; (-)-sparteine In diethyl ether; cyclohexane at -78℃; for 3h;
Stage #2: carbon dioxide In diethyl ether; cyclohexane for 0.333333h;
7%
(R)-phenylglycine
875-74-1

(R)-phenylglycine

diethyl 2-tert-butoxycarbonyloxyiminomalonate
59577-27-4

diethyl 2-tert-butoxycarbonyloxyiminomalonate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With triethylamine In methanol; water Ambient temperature;
(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol
188200-11-5

(2S,3R)-3-((tert-butoxycarbonyl)amino)-3-phenyl-1,2-propanediol

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With ruthenium trichloride; sodium periodate In tetrachloromethane; water; acetonitrile for 2h;
carbon dioxide
124-38-9

carbon dioxide

N-(trimethylsilyl)-N-(tert-butyloxycarbonyl)benzylamine
186375-60-0

N-(trimethylsilyl)-N-(tert-butyloxycarbonyl)benzylamine

A

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

B

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid
2900-27-8

(2S)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoic acid

Conditions
ConditionsYield
With sec.-butyllithium; (-)-sparteine In hexane at -78℃; for 0.333333h; Yield given. Yields of byproduct given. Title compound not separated from byproducts;
Stage #1: N-(trimethylsilyl)-N-(tert-butyloxycarbonyl)benzylamine With sec.-butyllithium; (-)-sparteine In cyclohexane; toluene at -78℃; for 3h;
Stage #2: carbon dioxide In cyclohexane; toluene for 0.333333h; Title compound not separated from byproducts;
Boc-D-PhGly-ONp

Boc-D-PhGly-ONp

A

4-nitro-phenol
100-02-7

4-nitro-phenol

B

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With phosphate buffer; apomyoglobin In 1,4-dioxane at 4℃; pH=7.0; Enzyme kinetics; Further Variations:; Reagents;
(2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal
137284-11-8, 138811-46-8, 140196-38-9

(2R)-2-N-(tert-butoxycarbonyl)amino-2-phenylethanal

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In water; tert-butyl alcohol at 20℃; for 2h;
tert-butyl [(1R)-2-nitro-1-phenylethyl]carbamate
685132-79-0

tert-butyl [(1R)-2-nitro-1-phenylethyl]carbamate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 24h;
With acetic acid; sodium nitrite In dimethyl sulfoxide at 40℃; for 24h; Inert atmosphere;
tert-butyl carbamate
4248-19-5

tert-butyl carbamate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: formic acid / methanol; H2O / 72 h / 20 °C
2: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating
3: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
4: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C
View Scheme
benzaldehyde
100-52-7

benzaldehyde

(E)-n-C6H13CH=CHZrCp2Cl

(E)-n-C6H13CH=CHZrCp2Cl

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: formic acid / methanol; H2O / 72 h / 20 °C
2: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating
3: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
4: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C
View Scheme
benzaldehyde N-boc imine
150884-50-7

benzaldehyde N-boc imine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
2: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C
View Scheme
tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate
155396-71-7

tert-butyl N-(phenyl(phenylsulfonyl)methyl)carbamate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: anhydrous potassium carbonate / tetrahydrofuran / 17 h / Heating
2: 81 percent / ethyldiisopropylamine; anhydrous zinc triflate; (-)-(1R,2S)-N-methylephedrine / molecular sieves 4 Angstroem / -20 °C
3: sodium nitrite; acetic acid / dimethylsulfoxide / 24 h / 40 °C
View Scheme
(E)-3-phenylpropenal
14371-10-9

(E)-3-phenylpropenal

(R)-p-mentha-1,5-diene

(R)-p-mentha-1,5-diene

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1.1: diethyl ether; pentane / 4 h / -100 - -78 °C
1.2: aq. NaOH; aq. H2O2 / diethyl ether; pentane / 14 h / -78 - 20 °C
1.3: pyridine / CH2Cl2 / 1 h / 0 °C
2.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C
3.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
3.2: tetrahydrofuran / 1 h / -42 - 20 °C
3.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
4.1: KOH / ethanol; H2O / 24 h / 20 °C
5.1: 1.1 g / diethyl ether / 3 h / 20 °C
6.1: O3 / CH2Cl2 / 3 h / -78 °C
6.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
7.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

1.) NaH; 2.) SOCl2

1.) NaH; 2.) SOCl2

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1.1 g / diethyl ether / 3 h / 20 °C
2.1: O3 / CH2Cl2 / 3 h / -78 °C
2.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
3.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
trans-(S)-1-phenyl-1,5-hexadien-3-ol
172925-28-9

trans-(S)-1-phenyl-1,5-hexadien-3-ol

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
1.2: tetrahydrofuran / 1 h / -42 - 20 °C
1.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
2.1: KOH / ethanol; H2O / 24 h / 20 °C
3.1: 1.1 g / diethyl ether / 3 h / 20 °C
4.1: O3 / CH2Cl2 / 3 h / -78 °C
4.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
5.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
(E)-(S)-1-Phenyl-hexa-2,5-dienylamine

(E)-(S)-1-Phenyl-hexa-2,5-dienylamine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1.1 g / diethyl ether / 3 h / 20 °C
2.1: O3 / CH2Cl2 / 3 h / -78 °C
2.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
3.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
(1S)-1-[(E)-2-phenylvinyl]but-3-enyl acetate

(1S)-1-[(E)-2-phenylvinyl]but-3-enyl acetate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: 2.0 g / K2CO3 / methanol / 3 h / 20 °C
2.1: NaN(SiMe3)2 / tetrahydrofuran / 0.5 h / -42 °C
2.2: tetrahydrofuran / 1 h / -42 - 20 °C
2.3: 89 percent / K2CO3 / xylene / 14 h / 150 °C
3.1: KOH / ethanol; H2O / 24 h / 20 °C
4.1: 1.1 g / diethyl ether / 3 h / 20 °C
5.1: O3 / CH2Cl2 / 3 h / -78 °C
5.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
6.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
tert-butyl (1S,2E)-1-phenylhexa-2,5-dienylcarbamate
849796-38-9

tert-butyl (1S,2E)-1-phenylhexa-2,5-dienylcarbamate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: O3 / CH2Cl2 / 3 h / -78 °C
1.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
2.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
2,2,2-trichloro-N-[(1S,2E)-1-phenylhexa-1,5-dienyl]acetamide
849796-21-0

2,2,2-trichloro-N-[(1S,2E)-1-phenylhexa-1,5-dienyl]acetamide

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: KOH / ethanol; H2O / 24 h / 20 °C
2.1: 1.1 g / diethyl ether / 3 h / 20 °C
3.1: O3 / CH2Cl2 / 3 h / -78 °C
3.2: Me2S / CH2Cl2 / 1.5 h / -78 - 20 °C
4.1: 2-methylbut-2-ene; NaClO2; NaH2PO4 / 2-methyl-propan-2-ol; H2O / 2 h / 20 °C
View Scheme
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / acetonitrile; H2O / 1 h / 0 °C
2: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C
3: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C
View Scheme
Multi-step reaction with 3 steps
1: 82 percent / diisopropylethylamine / dioxane / 20 h / 50 °C
2: 94 percent / H2 / Pd(OH)2 / methanol / 72 h / 760 Torr / Ambient temperature
3: NaIO4, RuCl3*H2O / acetonitrile; CCl4; H2O / 2 h
View Scheme
Multi-step reaction with 2 steps
1: 90 percent / H2 / Pd(OH)2/C / ethyl acetate
2: 79 percent / RuCl3, NaIO4, Na2CO3, / H2O; acetonitrile; CCl4 / 2 h / Ambient temperature
View Scheme
(R)-1-phenyl-2-(phenylmethoxy)ethylamine
162237-91-4

(R)-1-phenyl-2-(phenylmethoxy)ethylamine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: Et3N / acetonitrile; H2O / 1 h / 0 °C
2: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C
3: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C
View Scheme
(2-benzyloxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester
510730-65-1

(2-benzyloxy-1-phenyl-ethyl)-carbamic acid tert-butyl ester

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 96 percent / H2 / Pd(OH)2/C / methanol / 1 h / 20 °C
2: 77 percent / NaIO4; RuCl3*3H2O / CCl4; acetonitrile; H2O / 1 h / 0 - 20 °C
View Scheme
1-hydroxy-pyrrolidine-2,5-dione
6066-82-6

1-hydroxy-pyrrolidine-2,5-dione

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

N-(tert-butoxycarbonyl)-D-phenylglycine N-succinimido ester
39249-27-9

N-(tert-butoxycarbonyl)-D-phenylglycine N-succinimido ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In 1,4-dioxane100%
With dicyclohexyl-carbodiimide In tetrahydrofuran for 43h;98%
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide In N,N-dimethyl-formamide for 18h;
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl 4-aminophenethylcarbamate
94838-59-2

tert-butyl 4-aminophenethylcarbamate

(R)-[4-(2-tert-butoxycarbonylaminoethyl)phenylcarbamoyl]phenyl-methylcarbamic acid tert-butyl ester
849540-68-7

(R)-[4-(2-tert-butoxycarbonylaminoethyl)phenylcarbamoyl]phenyl-methylcarbamic acid tert-butyl ester

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0℃; for 1.58333h; Product distribution / selectivity;100%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In DMF (N,N-dimethyl-formamide) at 0 - 20℃; for 21.1667h; Product distribution / selectivity;
(R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate

(R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl ((R)-2-((R)-2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

tert-butyl ((R)-2-((R)-2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidin-1-yl)-2-oxo-1-phenylethyl)carbamate

Conditions
ConditionsYield
Stage #1: (R)-tert-butyl 2-(((2-(2-(methylthio)imidazo[2,1-b][1,3,4]thiadiazol-6-yl)benzo[d]oxazol-4-yl)oxy)methyl)pyrrolidine-1-carboxylate With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
Stage #2: Boc-D-Phg-OH 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 N,N-dimethyl-formamide at 20℃; for 1h;
100%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

4-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenyl)-2-((S)-1-t-butoxylcarbonylpyrrolidin-2-yl)imidazole

4-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenyl)-2-((S)-1-t-butoxylcarbonylpyrrolidin-2-yl)imidazole

(2S)-2-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenylimidazol-2-yl)-1-((R)-2-t-butoxycarbonylamino-2-phenylacetyl)pyrrolidine

(2S)-2-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenylimidazol-2-yl)-1-((R)-2-t-butoxycarbonylamino-2-phenylacetyl)pyrrolidine

Conditions
ConditionsYield
Stage #1: 4-(4-(trans-4-benzyloxycarbonylaminocyclohexyl)phenyl)-2-((S)-1-t-butoxylcarbonylpyrrolidin-2-yl)imidazole With hydrogenchloride In ethanol; chloroform; ethyl acetate at 20 - 60℃; for 2.5h;
Stage #2: Boc-D-Phg-OH With N-ethyl-N,N-diisopropylamine; HATU In ethyl acetate; N,N-dimethyl-formamide at 0℃; for 1h;
100%
morpholine
110-91-8

morpholine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl (R)-2-morpholino-2-oxo-1-phenylethylcarbamate

tert-butyl (R)-2-morpholino-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; dicyclohexyl-carbodiimide99%
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Inert atmosphere;
Stage #2: morpholine In dichloromethane for 12h; Inert atmosphere;
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

methylamine
74-89-5

methylamine

tert-butyl (R)-(methylcarbamoyl)(phenyl)methylcarbamate

tert-butyl (R)-(methylcarbamoyl)(phenyl)methylcarbamate

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran; water at -20℃; for 1h;99%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: methylamine In tetrahydrofuran at -20℃; for 2h;
96%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: methylamine In tetrahydrofuran; water at -20℃; for 2h;
96%
N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride

N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl (1R)-2-(4-(((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate

tert-butyl (1R)-2-(4-(((2Z)-3-methyl-2-(methylimino)-2,3-dihydro-1,3-thiazol-4-yl)methyl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h;
Stage #2: N-((2Z)-3-methyl-4-(-1-piperazinylmethyl)-1,3-thiazol-2(3H)-ylidene)methanamine trihydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine at 20℃; for 15h;
99%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

benzyl 7β-amino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylate
75460-19-4

benzyl 7β-amino-3-methyl-1,2-dehydro-1-carba-1-dethia-3-cephem-4-carboxylate

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methyl-8-oxo-1-aza-bicyclo[4.2.0]octa-2,4-diene-2-carboxylic acid

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-methyl-8-oxo-1-aza-bicyclo[4.2.0]octa-2,4-diene-2-carboxylic acid

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran for 1h; Ambient temperature;98%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(1R,2R)-(-)-trans-2-pyrrolidinyl-N-methylcyclohexylamine
67347-43-7

(1R,2R)-(-)-trans-2-pyrrolidinyl-N-methylcyclohexylamine

{(R)-[Methyl-((1R,2R)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester
125073-01-0

{(R)-[Methyl-((1R,2R)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Ambient temperature;97%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine
67198-53-2

trans-N-methyl-2-(1-pyrrolidinyl)-cyclohexanamine

{(R)-[Methyl-((1S,2S)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester
125072-99-3

{(R)-[Methyl-((1S,2S)-2-pyrrolidin-1-yl-cyclohexyl)-carbamoyl]-phenyl-methyl}-carbamic acid tert-butyl ester

Conditions
ConditionsYield
With pyridine; dicyclohexyl-carbodiimide In dichloromethane for 0.166667h; Ambient temperature;97%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid
70491-05-3

(2R)-[(tert-butoxycarbonyl)-amino](cyclohexyl)ethanoic acid

Conditions
ConditionsYield
With hydrogen In ethyl acetate at 80℃; under 7600.51 Torr; for 48h; Autoclave;97%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

11-aminoundecanoic acid methyl ester hydrochloride
29833-32-7

11-aminoundecanoic acid methyl ester hydrochloride

methyl 11-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoyl}amino)undecanoate
805230-91-5

methyl 11-({(2R)-2-[(tert-butoxycarbonyl)amino]-2-phenylethanoyl}amino)undecanoate

Conditions
ConditionsYield
With dmap; triethylamine; dicyclohexyl-carbodiimide In dichloromethane at 20℃;96%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside
124780-55-8

methyl 6,7-anhydro-2,3-di-O-benzyl-8-deoxy-α-D-threo-D-galacto-octopyranoside

methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-(2-t-butoxycarbonylamino-2-phenylacetyl)-8-deoxy-α-D-threo-D-galacto-octoside
131751-03-6

methyl 6,7-anhydro-2,3-di-O-benzyl-4-O-(2-t-butoxycarbonylamino-2-phenylacetyl)-8-deoxy-α-D-threo-D-galacto-octoside

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In tetrachloromethane for 3h;95%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

N,O-dimethylhydroxylamine*hydrochloride
6638-79-5

N,O-dimethylhydroxylamine*hydrochloride

2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide
819796-91-3

2(R)-N-(tert-butoxycarbonyl)-N'-methoxy-N'-methylphenylglycinamide

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃;94%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;52%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine In N,N-dimethyl-formamide at 20℃; for 2h;52%
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In acetonitrile at 0 - 20℃;
Stage #1: Boc-D-Phg-OH With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 2h;
Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In tetrahydrofuran; N,N-dimethyl-formamide at 20℃; for 18.5h; Cooling;
2,2-dimethylpropylamine
5813-64-9

2,2-dimethylpropylamine

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(R)-2-N-Boc-N-neopentyl-2-phenylacetamide

(R)-2-N-Boc-N-neopentyl-2-phenylacetamide

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: 2.2-dimethylpropylamine In tetrahydrofuran at -20℃; for 2h;
94%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: 2.2-dimethylpropylamine In tetrahydrofuran; water at -20℃; for 2h;
94%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

C14H21N3OS

C14H21N3OS

tert-butyl (R)-2-((S)-2-(4-cyclohexylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

tert-butyl (R)-2-((S)-2-(4-cyclohexylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h;
Stage #2: C14H21N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;
93.1%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(6R,7S)-7-Amino-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
62284-41-7, 73951-73-2

(6R,7S)-7-Amino-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
76284-31-6

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-3-(1-methyl-1H-tetrazol-5-ylsulfanylmethyl)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran93%
5-methyl-2-(piperazin-1-yl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one
856417-67-9

5-methyl-2-(piperazin-1-yl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate
856417-24-8

tert-butyl 2-(4-(5-methyl-3-oxo-1H-imidazo[1,5-c]imidazol-2(3H)-yl)-1-piperidinyl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h;
Stage #2: 5-methyl-2-(piperazin-1-yl)-1,2-dihydro-3H-imidazo[1,5-c]imidazol-3-one With triethylamine In acetonitrile at 20℃; for 15h; Product distribution / selectivity;
93%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

N-butylamine
109-73-9

N-butylamine

(R)-2-N-Boc-N-(n-butyl)-2-phenylacetamide

(R)-2-N-Boc-N-(n-butyl)-2-phenylacetamide

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: N-butylamine In tetrahydrofuran at -20℃; for 2h;
93%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: N-butylamine In tetrahydrofuran; water at -20℃; for 2h;
93%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butylamine
75-64-9

tert-butylamine

(R)-t-butyl (2-(t-butylamino)-2-oxo-1-phenylethyl)carbamate
926293-43-8

(R)-t-butyl (2-(t-butylamino)-2-oxo-1-phenylethyl)carbamate

Conditions
ConditionsYield
With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at 0 - 20℃; for 18h; Inert atmosphere;93%
Stage #1: Boc-D-Phg-OH With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -20℃; for 0.0833333h;
Stage #2: tert-butylamine In tetrahydrofuran at -20℃; for 2h;
74%
C12H19N3OS

C12H19N3OS

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl (R)-2-((S)-2-(4-tert-butylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

tert-butyl (R)-2-((S)-2-(4-tert-butylthiazol-2-ylcarbamoyl)-pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h;
Stage #2: C12H19N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;
92.9%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

(2R,4S,5R)-1-benzyl-2-((S)-hydroxy(quinolin-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide

O(9)-Boc-D-phenylglycineyl-N-benzylcinchoninium bromide

O(9)-Boc-D-phenylglycineyl-N-benzylcinchoninium bromide

Conditions
ConditionsYield
With dmap; dicyclohexyl-carbodiimide In dichloromethane at 0 - 20℃;92.7%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(6R,7S)-7-Amino-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

(6R,7S)-7-Amino-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester
76284-38-3

(6R,7S)-7-((R)-2-tert-Butoxycarbonylamino-2-phenyl-acetylamino)-8-oxo-1-aza-bicyclo[4.2.0]oct-2-ene-2-carboxylic acid benzyl ester

Conditions
ConditionsYield
With N-ethoxycarbonyl-2-ethoxy-1,2-dihydroquinoline In tetrahydrofuran92%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

C30H36N4O7

C30H36N4O7

Boc-D-Phg-D-Asp(OBn)-D-Pro-Acpc-Phe-OMe, Phg - 2-amino-2-phenylacetic acid, Acpc - 1-aminocyclopropane carboxylic acid

Boc-D-Phg-D-Asp(OBn)-D-Pro-Acpc-Phe-OMe, Phg - 2-amino-2-phenylacetic acid, Acpc - 1-aminocyclopropane carboxylic acid

Conditions
ConditionsYield
With 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20 - 23℃; for 12h;92%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

C9H13N3OS

C9H13N3OS

tert-butyl (R)-2-((S)-2-(4-methylthiazol-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

tert-butyl (R)-2-((S)-2-(4-methylthiazol-2-ylcarbamoyl)pyrrolidin-1-yl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol In dichloromethane at 20℃; for 0.166667h;
Stage #2: C9H13N3OS With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 18h;
91.2%
methanol
67-56-1

methanol

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

D-phenylglycine methyl ester hydrochloride
19883-41-1

D-phenylglycine methyl ester hydrochloride

Conditions
ConditionsYield
With chloro-trimethyl-silane at 20℃; for 45h; Esterification; de-tert-butoxycarbonylation;91%
Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

(5R,6R,1'S)-6-amino-1-[1-(naphthalen-1-yl)ethyl]-1-azaspiro[4.4]nonan-2-one
768370-32-7

(5R,6R,1'S)-6-amino-1-[1-(naphthalen-1-yl)ethyl]-1-azaspiro[4.4]nonan-2-one

(1R,6'R,1''R)-{[1-(1-naphthalen-2-ylethyl)-2-oxo-1-azaspiro[4.4]non-6-ylcarbamoyl]phenylmethyl}carbamic acid tert-butyl ester

(1R,6'R,1''R)-{[1-(1-naphthalen-2-ylethyl)-2-oxo-1-azaspiro[4.4]non-6-ylcarbamoyl]phenylmethyl}carbamic acid tert-butyl ester

Conditions
ConditionsYield
With dicyclohexyl-carbodiimide In dichloromethane at 20℃; for 1.5h;91%
2-methyl-5-(1-piperazinyl)imidazo[1,2-a]pyridine dihydrochloride

2-methyl-5-(1-piperazinyl)imidazo[1,2-a]pyridine dihydrochloride

Boc-D-Phg-OH
33125-05-2

Boc-D-Phg-OH

tert-butyl (1R)-2-(4-(2-methylimidazo[1,2-a]pyridin-5-yl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate
856418-67-2

tert-butyl (1R)-2-(4-(2-methylimidazo[1,2-a]pyridin-5-yl)-1-piperazinyl)-2-oxo-1-phenylethylcarbamate

Conditions
ConditionsYield
Stage #1: Boc-D-Phg-OH With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In acetonitrile at 20℃; for 0.25h;
Stage #2: 2-methyl-5-(1-piperazinyl)imidazo[1,2-a]pyridine dihydrochloride With 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine In acetonitrile at 20℃; for 15h;
91%

33125-05-2Downstream Products

33125-05-2Relevant articles and documents

Stille coupling of stereochemically defined α- sulfonamidoorganostannanes

Kells, Kevin W.,Chong, J. Michael

, p. 15666 - 15667 (2004)

Addition of tributylstannylmetallics to (R)-tert-butanesulfonimine derivatives of arylaldehydes provides α-sulfinamidostannanes with high (>98% de) diastereoselectivities. Oxidation of these compounds with m-CPBA gives α-sulfonamidostannanes which undergo Pd/Cu-catalyzed Stille-type couplings with benzoyl chloride. Best yields are achieved using the electron-rich tris(2,4,6-trimethoxyphenyl)phosphine as the ligand. Inversion of configuration at the benzylic carbon is observed. Copyright

Discovery of M3Antagonist-PDE4 Inhibitor Dual Pharmacology Molecules for the Treatment of Chronic Obstructive Pulmonary Disease

Armani, Elisabetta,Rizzi, Andrea,Capaldi, Carmelida,De Fanti, Renato,Delcanale, Maurizio,Villetti, Gino,Marchini, Gessica,Pisano, Anna Rita,Pitozzi, Vanessa,Pittelli, Maria Gloria,Trevisani, Marcello,Salvadori, Michela,Cenacchi, Valentina,Puccini, Paola,Amadei, Francesco,Pappani, Alice,Civelli, Maurizio,Patacchini, Riccardo,Baker-Glenn, Charles A.G.,Van De Po?l, Hervé,Blackaby, Wesley P.,Nash, Kevin,Amari, Gabriele

supporting information, p. 9100 - 9119 (2021/07/19)

In this paper, we report the discovery of dual M3 antagonist-PDE4 inhibitor (MAPI) compounds for the inhaled treatment of pulmonary diseases. The identification of dual compounds was enabled by the intuition that the fusion of a PDE4 scaffold derived from our CHF-6001 series with a muscarinic scaffold through a common linking ring could generate compounds active versus both the transmembrane M3 receptor and the intracellular PDE4 enzyme. Two chemical series characterized by two different muscarinic scaffolds were investigated. SAR optimization was aimed at obtaining M3 nanomolar affinity coupled with nanomolar PDE4 inhibition, which translated into anti-bronchospastic efficacy ex vivo (inhibition of rat trachea contraction) and into anti-inflammatory efficacy in vitro (inhibition of TNFα release). Among the best compounds, compound 92a achieved the goal of demonstrating in vivo efficacy and duration of action in both the bronchoconstriction and inflammation assays in rat after intratracheal administration.

Synthesis, characterization and antimicrobial activity of some novel 1-substituted benzimidazole derivatives

Astley, Demet,Isik, Erkut,Yasa, Ihsan,Yuksekdanaci, Seda

, p. 1372 - 1379 (2020/10/06)

Background: Benzimidazole derivatives are an important class of heterocyclic compounds in organic chemistry as they are related to a wide range of biological properties, including antimicrobial activity. Methods: A series of 1-naphthoyl and benzoyl benzimidazole derivatives were synthesised, identified and screened for their antimicrobial activities against a number of different test organisms such as Escherichia coli, Pseudomonas aureginosa, Klebsiella pneumoniae, Staphylococcus aureus, En-terococcus faecalis, Bacillus cereus, Salmonella typhimurium, Candida albicans (yeast). Results and Discussion: Benzimidazole derivatives (3a-d) were synthesised by using 4 different aminoacids. L-methionine, L-isoleucine, D-Phenylysine and L-Phenylamine as starting materials in the study. Experimental studies involve the use of benzimidazole derivatives (3a-d) of the selected amino acids to synthesize the benzoyl and naphthoyl derivatives of benzimidazole (4a-d, 5a-c). The structures of the synthesized compounds were confirmed by spectroscopic analyses (FTIR,1H-NMR,13C-NMR) and elemental analysis. Conclusion: In this study, only one compound (5a) showed a low MIC value against the eukaryotic microorganism C. albicans. The other six compounds showed higher antimicrobial activities against the prokaryotes C. albicans which is a normal flora in the mouth but is one of the organisms that cause infections leading to the weakening of the human immune system. Compound 5a is a can-didate for future alternative antimicrobial drugs against C. albicans infections. In addition, compound 5a has a potential to be used as an inhibitor against P. aureginosa for the treatment of cyst-ic fibrosis.

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