194933-36-3

Basic information

• Product Name: 1-Pyrrolidinecarboxylic acid, 2-[[(2S)-2-methyl-5-oxo-1-pyrrolidinyl]carbonyl]-, phenylmethyl ester, (2S)-
• CAS NO: 194933-36-3
• Molecular Formula: C18H22N2O4
• Molecular Weight: 330.37800
• Mol File: 194933-36-3.mol
• Article Data: 3

Chemical Properties

• CAS DataBase Reference: 1-Pyrrolidinecarboxylic acid, 2-[[(2S)-2-methyl-5-oxo-1-pyrrolidinyl]carbonyl]-, phenylmethyl ester, (2S)-(CAS DataBase Reference)
• NIST Chemistry Reference: 1-Pyrrolidinecarboxylic acid, 2-[[(2S)-2-methyl-5-oxo-1-pyrrolidinyl]carbonyl]-, phenylmethyl ester, (2S)-(194933-36-3)
• EPA Substance Registry System: 1-Pyrrolidinecarboxylic acid, 2-[[(2S)-2-methyl-5-oxo-1-pyrrolidinyl]carbonyl]-, phenylmethyl ester, (2S)-(194933-36-3)

Safety Data

• Hazardous Substances Data: 194933-36-3(Hazardous Substances Data)

Upstream product

• 1558-60-7 (5S)-5-methylpyrrolidin-2-one 
• 17543-45-2 Z-Pro-OPfp 
• 1148-11-4 N-Benzyloxycarbonyl-L-proline 

Relevant articles and documents

Developing microcolin A analogs as biological probes

Three microcolin A and B analogs have been synthesized. Their biological activity profiles were evaluated against several cell lines, revealing the existence of a structural determinant whose role in mediating the antiproliferative effect of the microcoli

Synthesis of Microcolin B, a Potent New Immunosuppressant Using an Efficient Mixed Imide Formation Reaction

Microcolin B, a potent new immunosuppressant isolated from blue-green alga Lyngbya majuscula off the Venezuelan coast, has been made using a methyl-directed asymmetric hydrogenation reaction with rhodium on alumina catalyst on lactone 4 for the synthesis of the key (R,R)-2,4-dimethyl-octanoic acid fragment 1. A new, direct mixed imide formation reaction was also developed for the production of the unusual prolylpyrrolen-2-one 2 portion of microcolin. The pentafluorophenyl ester of CBZ-proline 5 was reacted with the lithium imidate of lactam 6, providing the mixed imide in 80% yield. Coupling of acid 1 with the N-terminus of the tripeptide, followed by coupling with pyrrolylproline 2, gave microcolin B. The new mixed-imide forming reaction was also applied to a formal total synthesis of microcolin A. The pentafluorophenyl ester of TBS-protected cis-hydroxyproline was coupled with lactam 6, and the resultant imide was converted to the key pyrrolylproline made previously for microcolin A.