S 98 Synthesis of 4-amino derivatives of 5-oxoproline [Text] / V. P. Krasnov, A. Yu. Vigorov, I. A. Nizova, T. V. Matveeva, A. N. Grishakov, I. V. Bazhov, A. A. Tumashov, M. A. Ezhikova, M. I. Kodess // European Journal of Organic Chemistry. - 2007. - № 25. - P4257-4266 Рубрики: ХИМИЧЕСКИЕ НАУКИ Аннотация: 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 (2S,4RS)-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. |