Preparation of β-lactams and intermediates therefor

Claim 1

Process for the preparation of β-lactams of the formulae: ##STR33## wherein R' is selected from the group consisting of lower alkyl, aryl and aryl(lower alkyl), R" is selected from the group consisting of hydrogen and lower alkyl or R' and R" together with the carbon atoms to which they are attached are lower cycloalkyl and R''' is selected from the group consisting of lower alkyl and --OR, wherein R is lower alkyl, Y 1 is selected from the group consisting of hydrgen, furyl, phenyl, optionally substituted by methoxy or dimethylamino, styryl, optionally esterified carboxy and hydroxymethylene, X 1 is slected from the group consisting of hydrogen and methylthio or X 1 together with Y 1 is 1,5-pentylene, Z 1 is selected from the group consisting of hydrogen, methyl optionally substituted by phenyl and phenyl optionally substituted with at least one member of the group consisting of halogen, methyl, methoxy, methylthio and dimethylamino, or Z 1 is ##STR34## wherein R 5 is selected from the group, consisting of ethyl and ethylidene optionally substituted by optionally esterified hydroxy, R 6 is selected from the group consisting of hydrogen and carboxylic ester groups and R 1 is an acyl of an organic carboxylic acid of 1 to 8 carbon atoms, comprising reacting an 1,3-dicarbonyl compound of the formula: ##STR35## with glycine in the presence of a base MOH, wherein M is an alkali metal to form a vinylamino salt of the formula: ##STR36## activating the carboxyl group of the compound obtained with an activating agent selected from the group consisting of lower alkyl haloformate esters, di(lower alkyl) and diaryl phosphochloridates and cyanuric chloride, and reacting the activated compound in the presence of a tertiary base with an imino of the formula: ##STR37## to form the corresponding α-vinylamino-β-lactam of formula IV A and if desired, subjecting the compound thus obtained to mild acid hydrolysis to form the corresponding α-amino-βlactam of formula V A.