1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl ester

Base Information

• Chemical Name: 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl ester
• CAS No.: 75315-63-8
• Molecular Formula: C12H11NO4
• Molecular Weight: 233.224
• DSSTox Substance ID: DTXSID00396955
• Wikidata: Q82197934
• Mol file: 75315-63-8.mol

Synonyms:75315-63-8;1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl ester;benzyl 2,5-dioxopyrrolidine-1-carboxylate;N-(BENZYLOXYCARBONYL)SUCCINIMIDE;N-Cbz-succinimide;n-carbobenzoxysuccinimide;SCHEMBL274967;DTXSID00396955;N-(Benzyloxycarbonyl) succinimide;UTZLYIFQYGQUPA-UHFFFAOYSA-N;FT-0756813;A937167

Chemical Property of 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl ester

Chemical Property:

• XLogP3: 0.8
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 233.06880783
• Heavy Atom Count: 17
• Complexity: 317

Purity/Quality:

95+% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1CC(=O)N(C1=O)C(=O)OCC2=CC=CC=C2

Technology Process of 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl ester

There total 2 articles about 1-Pyrrolidinecarboxylic acid, 2,5-dioxo-, phenylmethyl 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: 79.0%

Succinimide (123-56-8,89963-74-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-(benzyloxycarbonyl)succinimide (75315-63-8)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃;

DOI:10.1080/00397911.2012.690061

Reference yield: 77.0%

N-chloro-succinimide (128-09-6) + L-proline methyl ester monohydrochloride (2133-40-6) + benzyl chloroformate (501-53-1,94274-21-2) → N-(benzyloxycarbonyl)succinimide (75315-63-8) + methyl N-benzyloxycarbonyl-4,5-dihydropyrrole-2-carboxylate (72978-22-4)

Guidance literature:

N-chloro-succinimide; L-proline methyl ester monohydrochloride; With triethylamine; In dichloromethane; at 0 - 20 ℃; for 2.5h;

benzyl chloroformate; With pyridine; In dichloromethane; at -20 ℃;

DOI:10.1021/ol102613z

Reference yield: 100.0%

C30H51N3O5 (1376616-31-7) + N-(benzyloxycarbonyl)succinimide (75315-63-8) → (1S,2S,4S)-4-(2-carbamoyl-2-methylpropyl-carbamoyl)-2-hydroxy-1-{(S)-2-[4-methoxy-3-(3-methoxypropoxy)-benzyl]-3-methylbutyl}-5-methylhexyl-carbamic acid benzyl ester (1236549-06-6)

Guidance literature:

With triethylamine; In dichloromethane; at 20 ℃; for 1h;

upstream raw materials:

N-chloro-succinimide

L-proline methyl ester monohydrochloride

benzyl chloroformate

Succinimide

Downstream raw materials:

tert-butyl N-(benzyloxycarbonyl)glycinate

3-<(benzyloxycarbonyl)aminomethyl>benzoic acid

diethyl 2-benzyloxycarbonylaminomalonate

3,2'-bis(N-benzyloxycarbonyl)-3',4',6'-trideoxy-6'-fluorokanamycin C

Refernces

• 1、 Huy, Peter,Neudoerfl, Joerg-Martin,Schmalz, Hans-Guenther. "A practical synthesis of trans -3-substituted proline derivatives through 1,4-addition". supporting information; experimental part. p. 216 - 219. Retrieved 2011/03/20.