Preparation of chiral 1,4-benzodiazepin-2-one-derivatives by reaction of (s)-α-amino acid chloride hydrochlorides etc.

Claim 1

A process preparing optically active 1,4-benzodiazepin-2-ones with (S)-configuration in the 3-position having the formula I ##STR5##wherein R 1 is a hydrogen atom, or a halogen atom, R 2 is an n- or iso- lower alkyl radical with at most 4 carbon atoms, a benzyl, p-hydroxybenzyl, or 3'-methyleneindolyl group, R 3 is a hydrogen atom or a halogen atom, comprising the steps of (a) reacting, in an inert solvent selected from methylene chloride and tetrahydrofuran at about room temperature, a compound of the formula II ##STR6##wherein R 1 and R 3 have the same significance as in Formula I with a compound of the formula III in the (S)-configuration ##STR7##in which R 2 has the same significance as in Formula I and Hal is a halogen atom, whereby an intermediate compound of the formula IV in the (S)-configuration is formed, and ##STR8## (b) cyclizing said intermediate compound in an inert solvent selected from the group consisting of a homogeneous mixture of water and an organic solvent and non-polar organic solvents, at a temperature of up to about 40° C whereby the compound of Formula I in the (S)-configuration is formed.