PROCESS FOR THE MANUFACTURE OF CHIRAL AZETIDINONES

摘要

Manufacture of chiral azetidinones of the general formula …… wherein R is an amino protecting group and M +/ &cir& is a cation, starting from L-ascorbic acid. Several alternatives lead, over a number of novel intermediates, to a novel intermediate of the formula …… wherein R and M +/ &cir& are as above and R<9>O- is a leaving group, which is treated with an alkali metal carbonate or bicarbonate, whereupon the compound of formula II is recovered from the reaction mixture. …The compounds of formula II are useful for preparing the new sulfazecin related antibiotic compound of the formula …… …This new antibiotic is similar in activity to the antibiotic azthreonam and useful in treating infectious diseases caused by gram negative microorganisms, particularly P. aeruginosa.