Process for the rearrangement of penicillins to cephalosporins a

Details Process for the rearrangement of penicillins to cephalosporins a Process for the rearrangement of penicillins to cephalosporins a

1975-08-07

1977-03-01

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424246, 2602391, 424271, C07D50110

Patent

active

040101568

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: 3725397 (1973-04-01), Graham et al.
patent: 3725399 (1973-04-01), Ellerton et al.
patent: 3843637 (1974-10-01), Rubinfield et al.
patent: 3896118 (1975-07-01), Ishimaru et al.

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