Process for the manufacture of optically uniform azetidinones

Details Process for the manufacture of optically uniform azetidinones Process for the manufacture of optically uniform azetidinones

C - Chemistry, Metallurgy

07

D

260/336

C07D 205/08 (2006.01) C07D 205/085 (2006.01) C07D 405/04 (2006.01) C07F 7/10 (2006.01)

Patent

CA 1251455

Abstract The optically uniform azetidinones of the general formula Image wherein R signifies benzyl, .beta.-(trimethyl- silyl)-lower alkyl or .beta.-halo-lower alkyl, R1 signifies a readily cleavable protecting group, R2 signifies a lower. optionally oxy- gen-containing, hydrocarbon group linked via a carbon, atom and R3 signifies a lower hydrocarbon group linked via a carbon atom, whereby R2 and R3 can also be linked with one another to form a ring, are valuable intermediates for the production of anti- microbially active .beta.-lactam antibiotics and can be manu- factured by reacting an alkali metal salt of a carboxylic acid of the general formula ROCONHCH2COOH II wherein R has the above significance, with an optically uniform compound of the general formula Image III wherein R1, R2 and R have the above significance, in the presence of a base and a sulphonic acid chloride of the general formula R4-SO2-C1 IV wherein R4 signifies phenyl, lower alkyl- phenyl, halophenyl, lower alkyl or halo- lower alkyl.

462331

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