(S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Base Information

• Chemical Name: (S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester
• CAS No.: 193269-79-3
• Molecular Formula: C11H21N3O3
• Molecular Weight: 243.30300
• DSSTox Substance ID: DTXSID601149467
• Mol file: 193269-79-3.mol

Synonyms:193269-79-3;(S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester;(S)-tert-Butyl 3-(2-aminoacetamido)pyrrolidine-1-carboxylate;Tert-butyl (3S)-3-[(2-aminoacetyl)amino]pyrrolidine-1-carboxylate;SCHEMBL7456395;BQNSQKNGVKRSAL-QMMMGPOBSA-N;DTXSID601149467;AM100456;(3s)-1-(tert-butoxycarbonyl)-3-(aminoacetylamino)pyrrolidine;(S)-tert-Butyl3-(2-aminoacetamido)pyrrolidine-1-carboxylate;tert-butyl (3S)-3-(2-aminoacetylamino)-1-pyrrolidinecarboxylate;(S)-3-(2-Aminoacetylamino)pyrrolidine-1-carboxylic acid tert-butyl ester;1,1-Dimethylethyl (3S)-3-[(2-aminoacetyl)amino]-1-pyrrolidinecarboxylate

Chemical Property of (S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

Chemical Property:

• PSA: 84.66000
• LogP: 1.09980
• XLogP3: -0.3
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 4
• Exact Mass: 243.15829154
• Heavy Atom Count: 17
• Complexity: 299

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(C)(C)OC(=O)N1CCC(C1)NC(=O)CN
• Isomeric SMILES: CC(C)(C)OC(=O)N1CC[C@@H](C1)NC(=O)CN

Technology Process of (S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester

There total 7 articles about (S)-3-(2-Amino-acetylamino)-pyrrolidine-1-carboxylic acid tert-butyl ester 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: 96.8%

(S)-tert-butyl 3-(2-bromoacetamido)pyrrolidin-1-carboxylate (1055268-63-7) → tert-butyl (3S)-3-(2-aminoacetylamino)-1-pyrrolidinecarboxylate (193269-79-3,1353960-31-2,1354019-55-8)

Guidance literature:

With ammonium hydroxide; sodium iodide; In methanol; water; at 20 ℃; for 48h;

Reference yield:

tert-butyl (S)-3-(2-chloroacetamido)pyrrolidine-1-carboxylate (335280-33-6,1353998-17-0) → tert-butyl (3S)-3-(2-aminoacetylamino)-1-pyrrolidinecarboxylate (193269-79-3,1353960-31-2,1354019-55-8)

Guidance literature:

With ammonia; In methanol; water; at 40 - 45 ℃; for 3.5h; Product distribution / selectivity;

Reference yield:

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine (147081-44-5) → tert-butyl (3S)-3-(2-aminoacetylamino)-1-pyrrolidinecarboxylate (193269-79-3,1353960-31-2,1354019-55-8)

Guidance literature:

Multi-step reaction with 2 steps

1: N-ethyl-N,N-diisopropylamine / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere

2: sodium iodide; ammonium hydroxide / water; methanol / 48 h / 20 °C

With ammonium hydroxide; N-ethyl-N,N-diisopropylamine; sodium iodide; In methanol; dichloromethane; water;

upstream raw materials:

tert-butyl (S)-3-(2-chloroacetamido)pyrrolidine-1-carboxylate

(3S)-3-amino-1-(tert-butoxycarbonyl)-pyrrolidine

di-tert-butyl dicarbonate

(R)-tert-butyl 3-hydroxypyrrolidine-1-carboxylate

Refernces

• 1、 -. "PROCESS FOR PRODUCING CARBAPENEM DERIVATIVE HAVING 1-ALKYLPYRROLIDINE STRUCTURE". Page/Page column 26. . Retrieved 2010/11/29.