3-Halo-cepham derivatives

Details 3-Halo-cepham derivatives 3-Halo-cepham derivatives

1973-04-19

1976-01-13

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, 2602391, 424271, C07D50118, C07D50110

Patent

active

039323986

ABSTRACT:
Penicillin sulfoxides are converted to 3-halo-3-methyl-cepham-4-carboxylic acid esters and amides or the corresponding cephem derivatives by heating the penicillin sulfoxide precursor in a polyhaloalkane solvent to a temperature between 50.degree. to about 150.degree.C. in the presence of an equimolar amount of a neutral or basic catalyst, respectively. The catalysts employed are bases such as pyridine, picoline, lutidine, quinoline, isoquinoline, dimethylaniline or a quaternary ammonium salt. The 3-halo-cepham intermediates produced with a quaternary ammonium catalyst are dehydrohalogenated to afford known cephem derivatives or converted to the free 4-carboxylic acid and the alkali metal, alkaline earth metal or ammonium salts thereof to afford novel antibacterial agents.

REFERENCES:
patent: 3275626 (1966-09-01), Morin et al.
patent: 3668201 (1972-06-01), Gutowski
patent: 3725397 (1973-04-01), Graham et al.
patent: 3725399 (1973-04-01), Ellerton et al.

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