Synthesis and rearrangement of potential zinc beta-lactamase inhibitors.

Van Hove, François;Vanwetswinkel, S.;Marchand-Brynaert, Jacqueline;Fastrez, Jacques
(1995) Tetrahedron Letters — Vol. 36, n° 51, p. 9313-9316 (1995)

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Authors
  • Van Hove, FrançoisUCLouvain
    Author
  • Vanwetswinkel, S.
    Author
  • Marchand-Brynaert, JacquelineUCLouvain
    Author
  • Fastrez, JacquesUCLouvain
    Author
Abstract
On alkylation of the p-toluene sulfonic salt of benzyl 6-aminopenicillanate (6-APA) with benzyl 2-bromoacetate, the benzyl esters of N-(benzyloxycarbonylmethyl)-6-APA (1) and of N,N-di(benzyloxycarbonylmethyl)-6-APA (3) were obtained. Hydrogenolysis of 1 on Pd/C afforded the N (carboxymethyl)-6-APA (2) while hydrogenolysis of 3 gave a rearranged product (4). Both 2 and 4 are inhibitors of the zinc beta-lactamase II of B. cereus.
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Van Hove, F., Vanwetswinkel, S., Marchand-Brynaert, J., & Fastrez, J. (1995). Synthesis and rearrangement of potential zinc beta-lactamase inhibitors. Tetrahedron Letters, 36(51), 9313-9316. https://doi.org/10.1016/0040-4039(95)02028-N (Original work published 1995)