Synthesis of 4‐Amino Derivatives of 5‐Oxoproline

Abstract

Abstract The possibility of obtaining the stereoisomeric derivatives of 5‐oxoproline and glutamic acid with a tertiary amino group at C‐4, using the nucleophilic substitution of bromine in dimethyl (2 S ,4 RS )‐4‐bromo‐ N ‐phthaloylglutamate with secondary amines followed by resolution of diastereomers and removal of protecting groups has been studied. We have shown that the reaction with arylamines results in optically pure 5‐oxoproline derivatives in high yields. In the case of more basic amines, the reaction is accompanied by racemization, and the target products can be isolated only as diastereomeric racemates.(© Wiley‐VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2007)