Stereospecific substitution of a hydroxy group by a chlorine atom in isomeric 2,3-disubstituted 3-hydroxytetrahydrothiophenes

Abstract

The stereospecific synthesis of the three possible isomers of 4-amino-3-chloro-2-(4-methoxycarbonylbutyl)tetrahydrothiophene hydrohalides from the corresponding isomers of 4-amino-3-hydroxytetrahydrothiophene by the action of thionyl chloride was realized. Three isomers of 4-ureido-3-chloro-2-(4-methoxycarbonylbutyl)tetrahydrothiophene were obtained from the 3-chlorotetrahydrothiophene derivatives. The configurations of the isomeric compounds obtained were proved by 1H and 13C NMR spectroscopy.