Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosp

Details Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosp Process for preparing 6-alkoxypenicillanic and 7-alkoxycephalosp

1973-10-04

1976-05-04

Coughlan, Jr., Paul M.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

260243C, 424246, 424271, C07D49904, C07D50104

Patent

active

039547310

ABSTRACT:
6-Acylamido-6-lower alkylthio (benzylthio) penicillanic and 7-acylamido-7-lower alkylthio (benzylthio)cephalosporanic and deacetoxycephalosporanic acid esters are reacted at a temperature between -80.degree. and -25.degree.C. with one equivalent of halogen to provide an intermediate halosulfonium halide which is reacted with a C.sub.1 -C.sub.4 lower alcohol, benzyl alcohol, p-nitrobenzyl alcohol or 2,2,2-trichloroethanol in the presence of a hydrogen halide acceptor to provide the corresponding 6- or 7- O-alkyl, benzyl, p-nitrobenzyl or 2,2,2-trichloroethyl penicillanic, cephalosporanic or deacetoxycephalosporanic acid esters. The 6- and 7- (2,2,2-trichloroethoxy) substituted penicillin or cephalosporin is reacted with zinc in formic acid to provide the 6- or 7-hydroxypenicillin or cephalosporin respectively.

REFERENCES:
patent: 3819621 (1974-06-01), Morimoto et al.
patent: 3842072 (1974-10-01), Heusler et al.

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