Hetacillin was oxidized with m-chloroperbenzoic acid to give the corresponding (R)- and (S)-sulfoxides. Ozonization of hetacillin not only oxidized the sulfide but caused unexpected oxidation of the imidazolidine ring to a 2H-imidazoline. The biological spectrum showed the (R)-sulfoxide to be appreciably more active than the (S)-sulfoxide.
Potassium 2 beta-(chloromethyl)-2 alpha-methylpenam-3 alpha-carboxylate 1,1-dioxide (BL-P2013) and its pivaloyloxymethyl ester were prepared by the conversion of 6-aminopenicillanic acid to p-nitrobenzyl 6 alpha-bromo-2,2-dimethylpenam-3 alpha-carboxylate 1-oxide, which was rearranged with benzoyl chloride and quinoline to p-nitrobenzyl 6 alpha-bromo-2 beta-(chloromethyl)-2 alpha-methylpenam-3 alpha-carboxylate in 65% yield. Oxidation and catalytic hydrogenation afforded BL-P2013, which was found to be a potent inhibitor of various bacterial beta-lactamases and has been found to protect amoxicillin from beta-lactamases in both in vitro and in vivo systems.
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