SYNTHÈSES D'ACIDES AMINOBUTYRIQUES: II. ACIDES ALKYLAMINO-2 HYDROXY-4 BUTYRIQUES

Abstract

Starting from 2-bromo-4-butyrolactone which was treated with primary amines, five new 2-alkylamino-4-hydroxy-N-alkylbutyramides were obtained in good yields. Acid hydrolysis gave the corresponding lactones, which, when treated with Ba(OH)2, gave the 2-alkylamino-4-hydroxybutyric acids. The new derivatives of homoserine thus prepared are: 2-methylamino-4-hydroxybutyric acid, 2-ethylamino-4-hydroxybutyric acid, 2-propylamino-4-hydroxybutyric acid, 2-butylamino-4-hydroxybutyric acid, and 2-cyclohexylamino-4-hydroxybutyric acid.Some of these amides were easily lactonized in HCl-acetone medium. Two 2-alkylamino-4-chloro-N-alkylbutyramides were also prepared.