US 4,375,434 AGranted

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

AssigneePfizer Inc.

InventorDavid L. Hageman

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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.

Claims6

Dependent claims

A process for preparing the compound of the formula ##STR10## or an acid addition salt thereof, which comprises:

(i) contacting a compound of the formula ##STR11## with from 0.5 to 1.5 molar equivalents of a compound of the formula ##STR12## in a reaction-inert organic solvent, at a temperature in the range from 0.degree.-60.degree. C., to give a compound of the formula ##STR13## and (ii) exposing the product of step (i) to aqueous or partially aqueous reaction conditions, at a pH in the range from 0.5 to 3.0, at a temperature in the range from 0.degree. to 30.degree. C., until conversion to an acid-addition salt of the compound of formula IV is substantially complete;
wherein R.sup.2 is selected from the group consisting of alkyl having 1 to 3 carbons, alkoxy having 1 to 3 carbons and phenyl, M is a carboxylate salt forming cation and X is selected from the group consisting of chloro, bromo, iodo, alkylsulfonyloxy having from 1 to 4 carbons, benzenesulfonyloxy and toluenesulfonyloxy.

Dependencies are inferred from the claim text.