7-Carboxy or 2,2,2-trichloroethoxy carbonyl- cephalosporins

Details 7-Carboxy or 2,2,2-trichloroethoxy carbonyl- cephalosporins 7-Carboxy or 2,2,2-trichloroethoxy carbonyl- cephalosporins

1972-07-03

1976-10-26

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, C07D50160

Patent

active

039883256

ABSTRACT:
6-APA, 7-ACA and 7-ADCA esters are reacted with benzaldehyde, acetophenone or substituted derivatives thereof providing imines which react in the presence of a strong base such as sodium hydride or lithium diisopropyl amide with a C.sub.2 -C.sub.5 alkanoyl halide, 2,2,2-trichloroethoxycarbonyl chloride, a benzoyl halide, a C.sub.1 -C.sub.4 alkoxycarbonyl chloride or a methoxymethyl halide to afford C.sub.6 and C.sub.7 substituted .beta.-lactam imines via acylation or methoxymethylation. The .beta.-lactam substituted imines are reacted with a carbonyl reagent, e.g. Girard's reagent T to provide a C.sub.6 substituted 6-APA ester or a C.sub.7 substituted 7-ACA or 7-ADCA ester which is acylated to provide a 6-acylamido-6-substituted penicillin or a 7-acyl-amide-7-substituted cephalosporin.

REFERENCES:
patent: 3709880 (1973-01-01), Goegelman et al.
patent: 3840533 (1974-10-01), Dolfini et al.

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