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7531-52-4 Usage

Chemical Properties

Crystalline

Uses

Different sources of media describe the Uses of 7531-52-4 differently. You can refer to the following data:
1. Proline based organocatalyst.
2. It is an important raw material and intermediate used in organic synthesis, pharmaceuticals, agrochemicals and dyestuff. Also it is a efficient organocatalysts for aldol reactions on water.

Definition

ChEBI: The carboxamide derivative of L-proline.

Check Digit Verification of cas no

The CAS Registry Mumber 7531-52-4 includes 7 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 4 digits, 7,5,3 and 1 respectively; the second part has 2 digits, 5 and 2 respectively.
Calculate Digit Verification of CAS Registry Number 7531-52:
(6*7)+(5*5)+(4*3)+(3*1)+(2*5)+(1*2)=94
94 % 10 = 4
So 7531-52-4 is a valid CAS Registry Number.
InChI:InChI=1/C5H10N2O/c6-5(8)4-2-1-3-7-4/h4,7H,1-3H2,(H2,6,8)/p+1/t4-/m1/s1

7531-52-4 Well-known Company Product Price

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  • TCI America

  • (P1382)  L-Prolinamide  >97.0%(T)

  • 7531-52-4

  • 1g

  • 205.00CNY

  • Detail
  • TCI America

  • (P1382)  L-Prolinamide  >97.0%(T)

  • 7531-52-4

  • 5g

  • 650.00CNY

  • Detail
  • TCI America

  • (P1382)  L-Prolinamide  >97.0%(T)

  • 7531-52-4

  • 25g

  • 1,990.00CNY

  • Detail
  • Alfa Aesar

  • (L20417)  L-(-)-Prolinamide, 99%   

  • 7531-52-4

  • 1g

  • 775.0CNY

  • Detail
  • Alfa Aesar

  • (L20417)  L-(-)-Prolinamide, 99%   

  • 7531-52-4

  • 5g

  • 3103.0CNY

  • Detail
  • Aldrich

  • (287059)  L-Prolinamide  98%

  • 7531-52-4

  • 287059-1G

  • 891.54CNY

  • Detail
  • Aldrich

  • (287059)  L-Prolinamide  98%

  • 7531-52-4

  • 287059-5G

  • 1,378.26CNY

  • Detail

7531-52-4SDS

SAFETY DATA SHEETS

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

Version: 1.0

Creation Date: Aug 12, 2017

Revision Date: Aug 12, 2017

1.Identification

1.1 GHS Product identifier

Product name L-prolinamide

1.2 Other means of identification

Product number -
Other names L-proline amide

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:7531-52-4 SDS

7531-52-4Synthetic route

Z-Pro-NH2
34079-31-7

Z-Pro-NH2

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With 10% palladium on carbon; hydrogen In methanol for 7h;100%
With hydrogen; palladium on activated charcoal In methanol for 9h; Ambient temperature;88.4%
With hydrogen; palladium on activated charcoal In methanol under 2068.6 Torr; for 5h;87%
With hydrogen; palladium In methanol for 3h;
N-acetyl-L-prolinamide
16395-58-7

N-acetyl-L-prolinamide

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With hydrogenchloride In water at 103℃; for 2h; Temperature;95.3%
L-proline methyl ester monohydrochloride
2133-40-6

L-proline methyl ester monohydrochloride

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With ammonia In methanol91%
With ammonia In methanol at 0 - 20℃; for 15h; Reagent/catalyst; Large scale;85%
With ammonia In methanol at -25℃; for 96h; Sealed tube;55%
methyl (2S)-pyrrolidine carboxylate
2577-48-2

methyl (2S)-pyrrolidine carboxylate

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With ammonia In methanol at 65℃; for 15h;90%
With methanol; ammonia
With ammonium hydroxide
With ammonium hydroxide In butan-1-ol at 5 - 30℃;
(2S,1'S)-1-(1'-phenylethyl)pyrrolidine-2-carboxamide
929897-95-0

(2S,1'S)-1-(1'-phenylethyl)pyrrolidine-2-carboxamide

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With hydrogen; palladium dihydroxide In ethanol; ethyl acetate at 20℃; under 760 Torr; for 14h;77%
(S)-(9H-fluoren-9-yl)methyl 2-carbamoylpyrrolidine-1-carboxylate
115134-39-9

(S)-(9H-fluoren-9-yl)methyl 2-carbamoylpyrrolidine-1-carboxylate

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With morpholine In N,N-dimethyl-formamide for 1h;73%
With alkylamine In N,N-dimethyl-formamide at 20℃; for 1h;
L-proline
147-85-3

L-proline

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Stage #1: L-proline With thionyl chloride In methanol for 2h; Heating;
Stage #2: With ammonia In methanol at 20℃; for 96h; Further stages.;
72%
Multi-step reaction with 3 steps
1: sodium hydroxide / H2O / Ambient temperature
2: 1.) triethylamine, isobutyl chloroformate, 2.) ammonia / 1.) chloroform, 0 deg C, 2 h, 2.) chloroform, RT, overnight
3: 88.4 percent / hydrogen / 10percent palladium on carbon / methanol / 9 h / Ambient temperature
View Scheme
Multi-step reaction with 2 steps
1: thionyl chloride / -5 - 70 °C
2: ammonium hydroxide / butan-1-ol / 5 - 30 °C
View Scheme
L-prolyl-L-alanine
6422-36-2

L-prolyl-L-alanine

A

(2R,5S)-2-Methyl-1,3-diazabicyclo<3.3.0>octan-4-on

(2R,5S)-2-Methyl-1,3-diazabicyclo<3.3.0>octan-4-on

B

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With ammonium acetate anodic oxidation; Pt electrodes, i = 370 mA*cm-2, current equiv.: 6.2 F/mol;A 49%
B 41%
ethyl (2S)-pyrrolidine-2-carboxylate
5817-26-5

ethyl (2S)-pyrrolidine-2-carboxylate

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With methanol; ammonia
(S)-2-Carbamoyl-pyrrolidine-1-carboxylic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester
125219-05-8

(S)-2-Carbamoyl-pyrrolidine-1-carboxylic acid 2-(4-methoxy-phenyl)-2-oxo-ethyl ester

A

1-(4-methoxyphenyl)ethanone
100-06-1

1-(4-methoxyphenyl)ethanone

B

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Irradiation; mild conditions;
(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate
35150-07-3

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With trifluoroacetic acid at 0℃; for 1h;
With trifluoroacetic acid acidolysis;
With trifluoroacetic acid In dichloromethane at 20℃; for 1h;
With trifluoroacetic acid In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere;
With trifluoroacetic acid In dichloromethane at 20℃; for 2h;
L-proline benzyl ester

L-proline benzyl ester

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With methanol; ammonia
Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Stage #1: Fmoc-Pro-OH With Rink amide resin; benzotriazol-1-ol; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0 - 20℃; for 3.5h;
Stage #2: With piperidine In N,N-dimethyl-formamide at 20℃; for 0.416667h;
Stage #3: With trifluoroacetic acid
Multi-step reaction with 2 steps
1: pyridine; di-tert-butyl dicarbonate; ammonium bicarbonate / 20 °C
2: alkylamine / N,N-dimethyl-formamide / 1 h / 20 °C
View Scheme
(2S,1'S)-5-hydroxy-2-(1'-phenylethylamino)pentanenitrile
929897-92-7

(2S,1'S)-5-hydroxy-2-(1'-phenylethylamino)pentanenitrile

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: NEt3; MsCl; DMAP / CH2Cl2 / 36 h / 0 - 20 °C
1.2: 3380 mg / aq. H2SO4 / CH2Cl2 / 48 h / 20 °C
2.1: 77 percent / H2 / Pd(OH)2/C / ethanol; ethyl acetate / 14 h / 20 °C / 760 Torr
View Scheme
Multi-step reaction with 2 steps
1: 78 percent / aq. H2SO4 / CH2Cl2 / 48 h / 20 °C
2: 77 percent / H2 / Pd(OH)2/C / ethanol; ethyl acetate / 14 h / 20 °C / 760 Torr
View Scheme
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

Boc-Thr(OBzl)-resin

Boc-Thr(OBzl)-resin

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 99 percent / Boc2O; pyridine; (NH4)2CO3 / dioxane / 18 h / 20 °C
2: TFA / CH2Cl2 / 1 h / 20 °C
View Scheme
Fmoc-Pro-OH
71989-31-6

Fmoc-Pro-OH

Fmoc-Arg(Pbf)-OH

Fmoc-Arg(Pbf)-OH

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: 88 percent / NH4HCO3; EEDQ / acetonitrile / 15 h / 20 °C
2: 73 percent / morpholine / dimethylformamide / 1 h
View Scheme
(S)-2-Ethoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid benzyl ester

(S)-2-Ethoxycarbonyloxycarbonyl-pyrrolidine-1-carboxylic acid benzyl ester

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1: NH3(gas) / CH2Cl2 / 1 h / -20 °C
2: 87 percent / H2 / 5percent Pd/C / methanol / 5 h / 2068.6 Torr
View Scheme
N-Benzyloxycarbonyl-L-proline
1148-11-4

N-Benzyloxycarbonyl-L-proline

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: N-methylmorpholine / CH2Cl2 / 2 h / -20 - -15 °C
2: NH3(gas) / CH2Cl2 / 1 h / -20 °C
3: 87 percent / H2 / 5percent Pd/C / methanol / 5 h / 2068.6 Torr
View Scheme
Multi-step reaction with 2 steps
1: 1.) triethylamine, isobutyl chloroformate, 2.) ammonia / 1.) chloroform, 0 deg C, 2 h, 2.) chloroform, RT, overnight
2: 88.4 percent / hydrogen / 10percent palladium on carbon / methanol / 9 h / Ambient temperature
View Scheme
water
7732-18-5

water

N-[[(Phenylmethoxy)-carbonyl]-D-phenylalanyl]-L-proline
17460-56-9

N-[[(Phenylmethoxy)-carbonyl]-D-phenylalanyl]-L-proline

isobutyl chloroformate
543-27-1

isobutyl chloroformate

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With 4-methyl-morpholine In tetrahydrofuran; ethyl acetate1.5 g (72%)
proline acid chloride
175446-63-6

proline acid chloride

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With ammonia In methanol at 20℃; for 72h;
(5S)-2,2-dimethyl-1,3-diazabicyclo<3.3.0>octan-4-one
97482-27-4

(5S)-2,2-dimethyl-1,3-diazabicyclo<3.3.0>octan-4-one

A

(2S)-N-propan-2-ylpyrrolidine-2-carboxamide
174089-62-4

(2S)-N-propan-2-ylpyrrolidine-2-carboxamide

B

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With sodium tetrahydroborate In methanol
(S)-Nα-(benzyloxycarbonyl)proline hydroxamic acid

(S)-Nα-(benzyloxycarbonyl)proline hydroxamic acid

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With palladium on activated charcoal; hydrogen In methanol
C6H11N2OPol

C6H11N2OPol

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
With trifluoroacetic acid In chloroform-d1 Inert atmosphere; solid phase reaction;
1-(tert-butoxycarbonyl)-L-proline
15761-39-4

1-(tert-butoxycarbonyl)-L-proline

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 4-methyl-morpholine; isobutyl chloroformate / tetrahydrofuran / 0.58 h / 0 °C
1.2: 4 h / 0 - 20 °C
2.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
View Scheme
(S)-acetylproline
68-95-1

(S)-acetylproline

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: thionyl chloride / dichloromethane / 6 h / 3 - 30 °C
2: ammonium hydroxide / dichloromethane / 3 h / 30 °C
3: hydrogenchloride / water / 2 h / 103 °C
View Scheme
L-glutamic acid
56-86-0

L-glutamic acid

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: sulfuric acid / 2 h / 1 - 25 °C
2.1: potassium borohydride / water / 4 h / 3 - 45 °C
3.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 1.5 h / -10 °C
3.2: 0.5 h / 25 °C
View Scheme
(S)-2-Amino-pentanedioic acid 5-ethyl ester
1119-33-1

(S)-2-Amino-pentanedioic acid 5-ethyl ester

L-prolinamide
7531-52-4

L-prolinamide

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: potassium borohydride / water / 4 h / 3 - 45 °C
2.1: chloroformic acid ethyl ester; triethylamine / dichloromethane / 1.5 h / -10 °C
2.2: 0.5 h / 25 °C
View Scheme
trifluoroacetic acid
76-05-1

trifluoroacetic acid

L-prolinamide
7531-52-4

L-prolinamide

Wang resin-linked N1-tert-butyloxycarbonyl-N2-triflylguanidine

Wang resin-linked N1-tert-butyloxycarbonyl-N2-triflylguanidine

(S)-1-Carbamimidoyl-pyrrolidine-2-carboxylic acid amide; compound with trifluoro-acetic acid

(S)-1-Carbamimidoyl-pyrrolidine-2-carboxylic acid amide; compound with trifluoro-acetic acid

Conditions
ConditionsYield
Stage #1: L-prolinamide; Wang resin-linked N1-tert-butyloxycarbonyl-N2-triflylguanidine In dichloromethane at 20℃;
Stage #2: trifluoroacetic acid In dichloromethane Further stages.;
100%
2-Bromoacetyl bromide
598-21-0

2-Bromoacetyl bromide

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2-bromoacetyl)pyrrolidine-2-carboxamide
253309-37-4

(S)-1-(2-bromoacetyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With dmap; triethylamine In dichloromethane for 2h; cooling;100%
Stage #1: 2-Bromoacetyl bromide; L-prolinamide In tetrahydrofuran at 0℃; for 0.5h;
Stage #2: With potassium carbonate In tetrahydrofuran at 0 - 20℃; for 4h;
85.8%
di-tert-butyl dicarbonate
24424-99-5

di-tert-butyl dicarbonate

L-prolinamide
7531-52-4

L-prolinamide

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate
35150-07-3

(S)-tert-butyl 2-carbamoylpyrrolidine-1-carboxylate

Conditions
ConditionsYield
In 1,4-dioxane; water at 20℃;100%
With triethylamine In dichloromethane at 0 - 20℃; for 6h;
With potassium carbonate In dichloromethane at 10 - 15℃; Inert atmosphere;
With triethylamine In dichloromethane at -15℃; for 12h; Concentration;
With N-benzyl-N,N,N-triethylammonium chloride; potassium carbonate In dichloromethane at 10 - 15℃; for 2h;
2,4-di-tertbutyl-6-chloromethylphenol
10193-84-7

2,4-di-tertbutyl-6-chloromethylphenol

L-prolinamide
7531-52-4

L-prolinamide

(2S)-1-(3,5-di-tert-butyl-2-hydroxybenzyl)pyrrolidine-2-carboxamide

(2S)-1-(3,5-di-tert-butyl-2-hydroxybenzyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With sodium hydrogencarbonate In acetonitrile for 24h; Inert atmosphere; Schlenk technique; Reflux;100%
N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine
4313-73-9

N-[N-[(phenylmethoxy)carbonyl]-L-phenylalanyl]-L-leucine

L-prolinamide
7531-52-4

L-prolinamide

Z-Phe-Leu-Pro-NH2

Z-Phe-Leu-Pro-NH2

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℃; for 18h;100%
2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carboxylic acid

2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carboxylic acid

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carbonyl)pyrrolidine-2-carboxamide

(S)-1-(2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carbonyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: 2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Inert atmosphere;
Stage #2: L-prolinamide In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;
99.7%
Stage #1: 2-((4-(4,6-bismorpholine-1,3,5-triazin-2-yl)phenyl)amino)-1H-benzo[d]imidazole-6-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.666667h; Inert atmosphere;
Stage #2: L-prolinamide In N,N-dimethyl-formamide at 80℃; for 8h; Inert atmosphere;
79%
fumaryl dichloride
627-63-4

fumaryl dichloride

L-prolinamide
7531-52-4

L-prolinamide

C14H16N4O2
913978-88-8

C14H16N4O2

Conditions
ConditionsYield
Stage #1: fumaryl dichloride; L-prolinamide With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h;
Stage #2: With trifluoroacetic anhydride In dichloromethane at 0 - 20℃; for 24 - 48h;
98%
3,5,5-trimethyl hexanal
5435-64-3

3,5,5-trimethyl hexanal

L-prolinamide
7531-52-4

L-prolinamide

(7aS)-3-(2,4,4-trimethylpentyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one
1378479-21-0

(7aS)-3-(2,4,4-trimethylpentyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one

Conditions
ConditionsYield
With triethylamine In methanol for 18h; Inert atmosphere; Reflux;98%
3-Phenylbutyraldehyde
16251-77-7

3-Phenylbutyraldehyde

L-prolinamide
7531-52-4

L-prolinamide

(7aS)-3-(2-phenylpropyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one
1084907-50-5

(7aS)-3-(2-phenylpropyl)hexahydro-1H-pyrrolo[1,2-c]imidazol-1-one

Conditions
ConditionsYield
With potassium carbonate In ethanol at 60℃; for 24h;97%
With potassium carbonate In ethanol at 60℃; for 24h; Inert atmosphere;97%
Z-Gly-(L)-Phe
1170-76-9

Z-Gly-(L)-Phe

L-prolinamide
7531-52-4

L-prolinamide

Z-Gly-L-Phe-L-Pro-NH2

Z-Gly-L-Phe-L-Pro-NH2

Conditions
ConditionsYield
With O-(3,4-dihydro-4-oxo-azabenzo-1,2,3-triazinyl)C(NMe2)2*PF6; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃;96.5%
With 2,4,6-trimethyl-pyridine; [(Me2N)(1H-1,2,3-triazolo[4,5-b]pyridinyl-1)CH=]Me2N*PF6 3-O In N,N-dimethyl-formamide96.5%
With 2,4,6-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; diisopropyl-carbodiimide In dichloromethane Condensation;94.8%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide
214398-99-9

(S)-1-(2-chloroacetyl) pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With triethylamine In dichloromethane at 5℃; for 2h; Reagent/catalyst; Inert atmosphere;96%
With triethylamine In dichloromethane at -5 - 0℃; for 0.5h; Inert atmosphere;96.3%
In tetrahydrofuran at 0℃; Reflux; Large scale;92%
cyclopropylcarbinyl bromide
7051-34-5

cyclopropylcarbinyl bromide

L-prolinamide
7531-52-4

L-prolinamide

(-)-(S)-1-cyclopropylmethyl-2-pyrrolidinecarboxamide
114812-44-1

(-)-(S)-1-cyclopropylmethyl-2-pyrrolidinecarboxamide

Conditions
ConditionsYield
With triethylamine In tetrahydrofuran for 24h;96%
BOC-glycine
4530-20-5

BOC-glycine

L-prolinamide
7531-52-4

L-prolinamide

(S)-tert-butyl 2-(2-carbamoylpyrrolidine-1-yl)-2-oxoethylcarbamate
52293-28-4

(S)-tert-butyl 2-(2-carbamoylpyrrolidine-1-yl)-2-oxoethylcarbamate

Conditions
ConditionsYield
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;95.8%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;95.8%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;95.8%
With benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine In N,N-dimethyl-formamide at 0 - 20℃;95.8%
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 3h;71%
(S)-N-(benzyloxycarbonyl)phenylglycine
5491-18-9, 17609-52-8, 53990-33-3, 60584-76-1

(S)-N-(benzyloxycarbonyl)phenylglycine

L-prolinamide
7531-52-4

L-prolinamide

Cbz-Phg-Pro-NH2

Cbz-Phg-Pro-NH2

Conditions
ConditionsYield
With N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 3-hydroxy-4-oxo-3,4-dihydro-5-azabenzo-1,2,3-triazine In chloroform; 2,2,2-trifluoroethanol at 20℃;95.4%
Stage #1: (S)-N-(benzyloxycarbonyl)phenylglycine With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 0℃; for 0.166667h;
Stage #2: L-prolinamide In N,N-dimethyl-formamide at 20℃; Further stages.;
93%
With 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; 1-diethoxyphosphinyloxy-7-azabenzotriazole92.8%
Z-Hle-OPfp

Z-Hle-OPfp

L-prolinamide
7531-52-4

L-prolinamide

Z-Hle-Pro-NH2

Z-Hle-Pro-NH2

Conditions
ConditionsYield
In N,N-dimethyl-formamide Ambient temperature;95%
(Sa)-3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthalene

(Sa)-3,3'-diformyl-2,2'-dihydroxy-1,1'-binaphthalene

L-prolinamide
7531-52-4

L-prolinamide

C32H30N4O4

C32H30N4O4

Conditions
ConditionsYield
In ethanol for 3h; Reflux;95%
2-chloro-6-(piperidin-1-ylmethyl)-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)thieno[2,3-d]pyrimidin-4-amine

2-chloro-6-(piperidin-1-ylmethyl)-N-(1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)thieno[2,3-d]pyrimidin-4-amine

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(6-(piperidin-1-ylmethyl)-4-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)thieno[2,3-d]pyrimidin-2-yl)pyrrolidine-2-carboxamide

(S)-1-(6-(piperidin-1-ylmethyl)-4-((1-(3,4,5-trimethoxyphenyl)-1H-imidazol-4-yl)amino)thieno[2,3-d]pyrimidin-2-yl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
In 1-methyl-pyrrolidin-2-one at 150℃; for 5h; Microwave irradiation;95%
1-chloro-2-(trifluoromethyl)benzene
88-16-4

1-chloro-2-(trifluoromethyl)benzene

L-prolinamide
7531-52-4

L-prolinamide

(S)-N'-((2-trifluoromethyl)phenyl)prolinylamide
403478-68-2

(S)-N'-((2-trifluoromethyl)phenyl)prolinylamide

Conditions
ConditionsYield
With 4-diphenylphosphino-13-dicyclohexylphosphino-[2.2]paracyclophane; water; palladium diacetate; caesium carbonate In 1,4-dioxane at 125℃; for 24h; Buchwald-Hartwig coupling;94%
(2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoyl)amino]-3-methylbutanoic acid
13123-00-7

(2S)-2-[((2S)-2-{[(benzyloxy)carbonyl]amino}-3-phenylpropanoyl)amino]-3-methylbutanoic acid

L-prolinamide
7531-52-4

L-prolinamide

Z-L-Phe-L-Val-L-Pro-NH2
164861-48-7

Z-L-Phe-L-Val-L-Pro-NH2

Conditions
ConditionsYield
With 1-hydroxy-7-aza-benzotriazole; [Me2N(1H-1,2,3-triazolo[4,5-b]pyridinyl)CH=]Me2N 3-oxide*PF6; 4-(N,N-dimethylamino)-2,6-di-tert-butylpyridine In N,N-dimethyl-formamide at 20℃;93.5%
With 2,4,6-trimethyl-pyridine; 1-hydroxy-7-aza-benzotriazole; 1-diethoxyphosphinyloxy-7-azabenzotriazole In N,N-dimethyl-formamide93.4%
With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide Product distribution; Further Variations:; Reagents;87.4%
4-oxo-1-pentyl-7-(phenylthio)-1,4-dihydroquinoline-3-carboxylic acid
1416564-42-5

4-oxo-1-pentyl-7-(phenylthio)-1,4-dihydroquinoline-3-carboxylic acid

L-prolinamide
7531-52-4

L-prolinamide

C26H29N3O3S
1416564-35-6

C26H29N3O3S

Conditions
ConditionsYield
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 18.5h; Inert atmosphere;93%
4-(5-((1-(2-ethyl-2-fluorobutyl)piperidin-4-yl)methyloxy)pyrimidin-2-yl)benzoic acid

4-(5-((1-(2-ethyl-2-fluorobutyl)piperidin-4-yl)methyloxy)pyrimidin-2-yl)benzoic acid

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(4-(5-((1-(2-ethyl-2-fluorobutyl)piperidin-4-yl)methoxy)pyrimidin-2-yl)benzoyl)pyrrolidine-2-carboxamide

(S)-1-(4-(5-((1-(2-ethyl-2-fluorobutyl)piperidin-4-yl)methoxy)pyrimidin-2-yl)benzoyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;93%
N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-N-phenylethenesulfonamide

N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-N-phenylethenesulfonamide

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2-(N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-N-phenylsulfamoyl)ethyl)pyrrolidine-2-carboxamide

(S)-1-(2-(N-(4-(5-(difluoromethyl)-1,3,4-oxadiazol-2-yl)benzyl)-N-phenylsulfamoyl)ethyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;92.9%
L-prolinamide
7531-52-4

L-prolinamide

L-proline
147-85-3

L-proline

Conditions
ConditionsYield
Stage #1: L-prolinamide With hydrogenchloride for 10h; Heating;
Stage #2: With methyloxirane In ethanol at 20℃; for 5h;
92%
chloroacetyl chloride
79-04-9

chloroacetyl chloride

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile
207557-35-5

(S)-1-(2-chloroacetyl)pyrrolidine-2-carbonitrile

Conditions
ConditionsYield
Stage #1: chloroacetyl chloride; L-prolinamide With potassium carbonate In acetonitrile at 0 - 15℃;
Stage #2: With trifluoroacetic anhydride at 0 - 15℃;
92%
Stage #1: chloroacetyl chloride; L-prolinamide With potassium carbonate In acetonitrile at 0 - 20℃;
Stage #2: With trifluoroacetic anhydride at 0 - 25℃;
92%
Stage #1: chloroacetyl chloride; L-prolinamide With trifluoroacetyl chloride In N,N-dimethyl-formamide at 50℃; for 1.5h;
Stage #2: With trifluoroacetyl chloride In N,N-dimethyl-formamide at 60℃; for 1.5h; Reagent/catalyst; Temperature;
83.4%
(2S)-2-[(t-butoxycarbonyl)amino]-3-{4-[(5-nitropyridin-2-yl)oxy]phenyl}propanoic acid
1011521-39-3

(2S)-2-[(t-butoxycarbonyl)amino]-3-{4-[(5-nitropyridin-2-yl)oxy]phenyl}propanoic acid

L-prolinamide
7531-52-4

L-prolinamide

(2S)-1-{(2S)-2-[(t-butoxycarbonyl)amino]-3-[4-(5-nitro pyridin-2-yloxy)phenyl]propanoyl}pyrrolidine-2-carboxamide

(2S)-1-{(2S)-2-[(t-butoxycarbonyl)amino]-3-[4-(5-nitro pyridin-2-yloxy)phenyl]propanoyl}pyrrolidine-2-carboxamide

Conditions
ConditionsYield
Stage #1: (2S)-2-[(t-butoxycarbonyl)amino]-3-{4-[(5-nitropyridin-2-yl)oxy]phenyl}propanoic acid With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; for 0.5h;
Stage #2: L-prolinamide In N,N-dimethyl-formamide at 20℃; for 15h;
92%
9-bromo-10-(bromomethyl)-2,3,6-trimethoxyphenanthrene
1215841-60-3

9-bromo-10-(bromomethyl)-2,3,6-trimethoxyphenanthrene

L-prolinamide
7531-52-4

L-prolinamide

(2S)-1-[(10-bromo-3,6,7-trimethoxy-9-phenanthryl)methyl]pyrrolidine-2-carboxamide
1309782-29-3

(2S)-1-[(10-bromo-3,6,7-trimethoxy-9-phenanthryl)methyl]pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux;92%
9-bromo-10-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene
1215841-59-0

9-bromo-10-(bromomethyl)-2,3,6,7-tetramethoxyphenanthrene

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide
1309782-28-2

(S)-1-[(9-bromo-2,3,6,7-tetramethoxyphenanthren-10-yl)methyl]pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux;92%
With potassium carbonate In N,N-dimethyl-formamide for 8h; Reflux;92%
2’-cyano-3-fluoro-4’-((1-(2-fluoro-2-methylpropyl)piperidin-4-yl)methoxy)biphenyl-4-carboxylic acid

2’-cyano-3-fluoro-4’-((1-(2-fluoro-2-methylpropyl)piperidin-4-yl)methoxy)biphenyl-4-carboxylic acid

L-prolinamide
7531-52-4

L-prolinamide

(S)-1-(2'-cyano-3-fluoro-4’-((1-(2-fluoro-2-methylpropyl)piperidin-4-yl)methoxy)biphenylcarbonyl)pyrrolidine-2-carboxamide

(S)-1-(2'-cyano-3-fluoro-4’-((1-(2-fluoro-2-methylpropyl)piperidin-4-yl)methoxy)biphenylcarbonyl)pyrrolidine-2-carboxamide

Conditions
ConditionsYield
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;92%
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In dichloromethane at 20℃; for 18h;92%

7531-52-4Relevant articles and documents

-

Takahashi,Cohen

, p. 864,865 (1969)

-

Preparation method of L-prolinamide

-

Paragraph 0039; 0041-0048, (2021/01/28)

The invention provides a preparation method of L-prolinamide. The preparation method comprises the following steps: by using L-proline as an initial raw material, firstly forming L-proline methyl ester hydrochloride, then carrying out ammonolysis to obtain a synthetic solution containing L-prolinamide, and dissociating the residual L-prolinamide hydrochloride in the synthetic solution into L-prolinamide through inorganic alkali in a non-aqueous environment, and removing by-products through a non-aqueous solvent system. According to the preparation method, the L-prolinamide hydrochloride can befully dissociated, the by-products and the impurities can be effectively removed, the yield and purity of the target product can be remarkably improved, the preparation method is simple and convenient in process, mild in condition and easy to control, expensive reagents are not needed, the production efficiency of the L-prolinamide can be improved, and the preparation method is suitable for large-scale industrial production and has important economic and social values.

Synthesis method of L-prolinamide

-

, (2019/01/16)

The invention belongs to the field of organic synthesis, and discloses a synthesis method of L-prolinamide. The method comprises steps of S1, dissolving an initial material, L-proline, in water and then reacting with acetic anhydride, after reaction, extracting and drying to prepare N-acetyl-L-proline; S2, in a solvent system, performing a reaction on a raw material, N-acetyl-L-proline prepared inS1 and thionyl chloride, then concentrating and drying to obtain a compound; S3, dripping aqueous ammonia in the compound prepared in S2 as a raw material so as to react, filtering and preparing 1-acetyl-2-pyrrolidinecarboxamide; and S4, dripping HC1 into the 1-acetyl-2-pyrrolidinecarboxamide prepared in S3 as a raw material, so as to react, then concentrating, filtering and drying to prepare L-prolinamide. In the reaction process of the synthesis method provided by the invention, common reagent raw materials are used, the costs are low, the reaction conditions are mild, the chiral purity ishigh, the yield is high, the environment pressure is low, and the synthesis method is suitable for large-scale production.

HEMIAMINAL-TAG FOR PROTEIN LABELING AND PURIFICATION

-

Page/Page column 22; 24, (2018/06/30)

The invention pertains to the synthesis, isolation, and characterization of hemiaminal for selective labeling of peptides, proteins, antibodies, and organic fragments with -C(=0) CH2NH2 and derivatives with -CH2NH2 group over -C(=0) CHRNH2 group (where R≠H). The invention also pertains to the method of single-site immobilization of proteins through N-terminus Gly on solid phase. The invention includes late-stage tagging of N-terminus Gly with an affinity tag, 19F NMR probe, and a fluorophore and a method for metal-free protein purification and isolation of analytically pure proteins.

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