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Synthesis of 4‐Amino Derivatives of 5‐Oxoproline
Author(s) -
Krasnov Victor P.,
Vigorov Alexey Yu.,
Nizova Irina A.,
Matveeva Tatyana V.,
Grishakov Alexander N.,
Bazhov Iliya V.,
Tumashov Andrey A.,
Ezhikova Marina A.,
Kodess Mikhail I.
Publication year - 2007
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/ejoc.200700346
Subject(s) - chemistry , diastereomer , racemization , protecting group , bromine , nucleophilic substitution , amino acid , nucleophile , organic chemistry , stereochemistry , medicinal chemistry , catalysis , biochemistry , alkyl
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)