Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-di

Details Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-di Process for 6'-amino-penicillanoyloxymethyl penicillanate 1,1-di

1982-06-21

1983-03-01

Rizzo, Nicholas S.

Chemistry of carbon compounds

Miscellaneous organic carbon compounds

C-metal

424270, 424271, 2602391, C07D49904

Patent

active

043754341

ABSTRACT:
6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is prepared by a two-step procedure. The first step consists of coupling a salt of a 6-(protected amino)penicillanic acid with a halomethyl, an alkylsulfonyloxymethyl or an arylsulfonyloxymethyl ester of penicillanic acid 1,1-dioxide, to give a 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide, wherein the protection at the 6-position has been achieved by coupling the 6-aminopenicillanic acid with a beta-dicarbonyl compound. The second step consists of removal of the protecting group on the 6'-amino group, using aqueous acid. 6'-Aminopenicillanoyloxymethyl penicillanate 1,1-dioxide is a chemical intermediate for preparing antibacterial agents. Also claimed are the 6'-(protected amino)penicillanoyloxymethyl penicillanate 1,1-dioxide compounds used as intermediates in the process of this invention.

REFERENCES:
patent: 4244951 (1981-01-01), Bigham
Dane and Dockner, Angewandte Chemie, Int. Edn. Eng., 3,439, (1964).
Dane and Dockner, Chem. Ber., 98, 789, (1965).

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