(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid
• CAS No.: 23500-10-9
• Molecular Formula: C7H10 Cl N O3
• Molecular Weight: 191.614
• Hs Code.: 2933998090
• European Community (EC) Number: 245-695-3
• Nikkaji Number: J228.979B
• Mol file: 23500-10-9.mol

Synonyms:Chloroac-pro-oh;(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid;23500-10-9;(S)-1-(2-Chloro-acetyl)-pyrrolidine-2-carboxylic acid;(2S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid;C7H10ClNO3;N-Chloroacetyl-L-proline;EINECS 245-695-3;Chloracetylprolin;N-a-Chloroacetyl-L-proline;N-(Chloroacetyl)-L-proline;SCHEMBL3200494;MFCD00046089;1-?(2-?Chloroacetyl)?-L-?proline;AKOS004121605;AKOS015850602;AMY202100055;CS-0165391;(S)-1-(2-Chloroacetyl)-pyrrolidine-2-carboxylic acid;(S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid? (Vildagliptin Impurity pound(c)

Chemical Property of (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid

Chemical Property:

• Vapor Pressure: 1.76E-07mmHg at 25°C
• Melting Point: 112-113 °C
• Boiling Point: 399°Cat760mmHg
• PKA: 3.27±0.20(Predicted)
• Flash Point: 195.1°C
• Density: 1.422g/cm³
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 2
• Exact Mass: 191.0349209
• Heavy Atom Count: 12
• Complexity: 207

Purity/Quality:

98%,99%, ^*data from raw suppliers

(S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(N(C1)C(=O)CCl)C(=O)O
• Isomeric SMILES: C1C[C@H](N(C1)C(=O)CCl)C(=O)O
• Uses: (S)-1-(2-Chloro-acetyl)-pyrrolidine-2-carboxylic Acid is used in preparation of vildagliptin impurity.

Technology Process of (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid

There total 4 articles about (S)-1-(2-Chloroacetyl)pyrrolidine-2-carboxylic acid which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

chloroacetyl chloride (79-04-9) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid (23500-10-9)

Guidance literature:

In tetrahydrofuran; at 90 ℃; for 2.75h; Cooling with ice;

DOI:10.2174/1570178611310030003

Reference yield:

chloroacetic acid (79-11-8) + L-proline (147-85-3,25191-13-3,37159-97-0,4305-67-3,4607-28-7) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid (23500-10-9)

Guidance literature:

In acetonitrile; at 20 ℃; for 48h;

DOI:10.1023/B:RUCB.0000011878.52263.c4

Reference yield:

pyrrolidine-2-carboxylic acid amide (2812-47-7) → (S)-1-(2-chloroacetyl)pyrrolidine-2-carboxylic acid (23500-10-9)

Guidance literature:

Multi-step reaction with 2 steps

1: amidase from pig's-kidneys / asymmetrische Hydrolyse

2: aqueous NaOH

With sodium hydroxide; amidase from pig's-kidneys;

upstream raw materials:

chloroacetyl chloride

L-proline

chloroacetic acid

pyrrolidine-2-carboxylic acid amide

Downstream raw materials:

H-Gly-Pro-OH

1-glycoloyl-L-proline amide

Benzoic acid 2-((S)-2-carbamoyl-pyrrolidin-1-yl)-2-oxo-ethyl ester

1-chloroacetyl-2-(S)-cyanopyrrolidine

Refernces

• 1、 Zhang, Li,Jiang, Lan,Guan, Xiaoshu,Cai, Linhong,Wang, Jingyu,Xiang, Peng,Pan, Junyi,Hu, Xiangnan. "A facile method to synthesize vildagliptin". . p. 305 - 309. Retrieved 2020/12/01.
• 2、 -. "Preparation process of vildagliptin impurity". Paragraph 0023-0025. . Retrieved 2021/01/04.