216315-22-9

Basic information

• Product Name: diphenylmethyl (2S)-6-oxopipecolate
• Synonyms: diphenylmethyl (2S)-6-oxopipecolate
• CAS NO: 216315-22-9
• Molecular Weight: 309.365
• Mol File: 216315-22-9.mol
• Article Data: 1

Chemical Properties

• CAS DataBase Reference: diphenylmethyl (2S)-6-oxopipecolate(CAS DataBase Reference)
• NIST Chemistry Reference: diphenylmethyl (2S)-6-oxopipecolate(216315-22-9)
• EPA Substance Registry System: diphenylmethyl (2S)-6-oxopipecolate(216315-22-9)

Safety Data

• Hazardous Substances Data: 216315-22-9(Hazardous Substances Data)

Upstream product

• 1118-90-7 L-homoglutamic acid 
• 908093-98-1 diazodiphenylmethane 
• 34622-39-4 (2S)-6-oxopipecolic acid 

Downstream Products

• 216301-91-6 diphenylmethyl (2S)-N-benzyloxycarbonyl-6-oxopipecolate 
• 259181-49-2 diphenylmethyl N-phenoxycarbonyl-6-oxopipecolate 
• 259181-47-0 diphenylmethyl N-tert-butoxycarbonyl-6-oxopipecolate 
• 259181-48-1 diphenylmethyl N-methoxycarbonyl-6-oxopipecolate 

Relevant articles and documents

Synthesis of a new dual metalloprotease inhibitor. I. Diastereoselective alkylation of protected 6-oxopipecolic acid esters

Diastereoselective methylation of the enolate generated from various protected 6-oxopipecolic acid esters (3aa-3cd) was studied. The protecting groups on the carboxylic acid and amino groups significantly influenced the trans/cis selectivity in the methylation reaction. The optimal substrate (3ca), bearing benzhydryl ester and carbobenzyloxy moieties gave a trans/cis isomer ratio of ca. 4:1. Investigation of the reaction conditions revealed that the reaction solvent, alkylating reagent, and base employed to generate the enolate, were decisive factors for diastereoselectivity. Further optimization of reaction conditions, including the amounts of the reagents and their addition sequence enabled maximization of reaction conversion and minimization of by-products to produce the trans rich 5-methyl-6-oxopipecolic acid ester (4ca) on a large scale.