Synthesis,stereochemistry and pharmacological activity of rac.-cis-tetrahydro-6-hydroxy-7-(4-methoxyphenyl)-1,4-thiazepin-5(2H)-ones

Reaction of 2-aminoethanethiol ( 3 ) with trans-3-(p-methoxyplienyl)glycidate ( 4 ) gave the rac.-cis-1,4-thiazepinone 5 and a by-product 6 . The structure of 5 was proven by X-ray crystallography. The X-ray data revealed that this compound adopts the chair conformation in the solid state and the heterocyclic ring is sevenmembered. The structure of the by-product 6 was elucidated on the basis of spectral data. Compounds 9 and 10 were inactive as calcium channel blocking agents.