Hydroxymethyl carbonate monopenicillanoyl intermediates

C - Chemistry – Metallurgy – 07 – D

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260/114.1

C07D 499/68 (2006.01)

Patent

CA 1236827

ABSTRACT OF THE DISCLOSURE Disclosed is a novel compound of the formula: Image (IV) wherein R1 is hydrogen, hydroxy, formyloxy, alkanoyloxy having from two to seven carbon atoms, alkoxycarbonyloxy having from two to seven carbon atoms or R2C6H4COO where R2 is hydrogen, alkyl having from one to four carbon atoms, alkoxy having from one to four carbon atoms, F, Cl, Br, I or CN; Q is a group readily convertible to amino; and X is Cl, Br or I, which can be produced by reacting a compound of the formula: Image (VI) where M is a carboxylate salt forming cation, and R1 and Q are as previously defined, with at least one equimolar amount of a compound of the formula XCH2OCOOCH2X, where X is as previously defined in a reaction inert organic solvent at a temperature of from -20 to 60°C. The compound (IV) is useful as an intermediate for producing an antimicrobial agent bis-ester of hydroxymethyl carbonate in which one hydroxy group is esterified with penicill- anic acid 1,1-dioxide and the other with an alpha-aminopenicillin.

502711

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