Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)...

Details Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)... Optical resolution of threo-2-hydroxy-3-(2-aminophenylthio)...

C - Chemistry, Metallurgy

07

C

C07C 323/62 (2006.01) C07C 319/28 (2006.01) C07C 323/56 (2006.01) C07D 453/04 (2006.01)

Patent

CA 2100022

D(+)-threo-2-hydroxy-3-(2-aminophenylthio)-3-(4-methoxyphenyl)propionic acid, an important intermediate in the synthesis of diltiazem hydrochloride, is obtained in better yields and high optical purity by a novel resolution process comprising the reaction of 2 moles of the (~) racemic acid with 1 mole of quinine and 1 mole of a base in a suitable polar solvent system to form a salt of the D(+) acid and quinine which precipitates; separating said salt and decomposing it with a strong base.

L'acide D(+)-thréo-2-hydroxy-3-(2-aminophénylthio)-3-(4-méthoxyphényl)propionique, un intermédiaire important de la synthèse du chlorhydrate de diltiazem, est obtenu avec de meilleurs rendements et une grande pureté optique à l'aide d'un nouveau procédé de résolution comprenant la réaction de 2 moles de l'acide (~) racémique avec 1 mole de quinine et 1 mole d'une base dans un système de solvant polaire approprié pour former un sel de D(+) acide et de quinine qui précipite ainsi que la séparation et la décomposition dudit sel avec une base forte.

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