Synthesis and beta-lactamase inhibitory properties of 2 beta-(chloromethyl)-2 alpha-methylpenam-3 alpha-carboxylic acid 1,1-dioxide.

@article{Gottstein1981SynthesisAB,
  title={Synthesis and beta-lactamase inhibitory properties of 2 beta-(chloromethyl)-2 alpha-methylpenam-3 alpha-carboxylic acid 1,1-dioxide.},
  author={Werner Gottstein and L. B. Crast and Roger G Graham and Ulric Haynes and Dennis N. McGregor},
  journal={Journal of medicinal chemistry},
  year={1981},
  volume={24 12},
  pages={
          1531-4
        }
}
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… CONTINUE READING