Process for the production of antibiotic penems

Details Process for the production of antibiotic penems Process for the production of antibiotic penems

1982-03-30

1984-04-17

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, 424271, 260239A, C07D49904, C07D49900

Patent

active

044433735

ABSTRACT:
There is disclosed a process for preparing 6-hydroxyethyl-2-alkylthio penem-3-carboxylates by a multi-step process comprising reacting an azetidinone having a protected hydroxy group at the 5 position with a diester of ketomalonic acid, chlorinating the resulting N-substituted azetidinone, removing the chlorine and OH protecting group, reacting the resulting compound with a silver salt to form a silver thio substituted at the 4 position of the azetidinone, cyclizing with a thiocarbonyl compound, then reacting the resulting penam with a fluoride to form a penam-penem tautomer, reacting the tautomer with a halide or ethylenically unsaturated compound followed by deprotecting the carboxyl at the 3 position to form the final penem product in high yield.

REFERENCES:
patent: 4282236 (1981-08-01), Broom
patent: 4283531 (1981-08-01), Ganguly et al.

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