Preparation of halomethyl esters (and related esters) of penicil

Details Preparation of halomethyl esters (and related esters) of penicil Preparation of halomethyl esters (and related esters) of penicil

1981-03-23

1983-12-06

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, C07D49900, A61K 31425

Patent

active

044192843

ABSTRACT:
Process for preparation of halomethyl esters (and related esters) of penicillanic acid 1,1-dioxide of the formula ##STR1## where X is Cl, Br, I, certain alkylsulfonyloxy or arylsulfonyloxy groups, useful as intermediates in production of antibiotics having beta-lactamase activity, which comprises hydrogenolysis of an ester of the formula ##STR2## where n is zero, 1 or 2; Y and Z are each Cl, Br or I, or Y is H and Z is Cl, Br, I, C.tbd.N-- or SCN--, or Y is arylselenyl and Z is Cl or Br; and when n is zero or 1, oxidation of the hydrogenolysis product; a process for preparing compounds of formula (VI, n=2) by oxidation of the corresponding compound (VI) wherein n is zero or 1, and certain novel intermediates useful in the above processes.

REFERENCES:
patent: 3996235 (1976-12-01), Bentley et al.
patent: 4224951 (1981-01-01), Bigham
patent: 4234579 (1980-11-01), Barth

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