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An efficient synthesis of (±) 7-oxo-3-thia-1-azabicyclo[3.2.0]heptane-2-carboxylate-3,3-dioxide

✍ Scribed by John Brennan; Ivan L. Pinto

Publisher
Elsevier Science
Year
1983
Tongue
French
Weight
115 KB
Volume
24
Category
Article
ISSN
0040-4039

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✦ Synopsis

The title compound was prepared in good yield via intramolecular insertion of an a-alkoxycarbonyl, a-sulphonyl carbene into the N-H bond of an azetidinone.

Esters of (k) 7-oxo-3-thia-l-azabicyclo[3.2.0lheptane-2-carboxylate-3,3-dioxide, 1, are potentially useful intermediates in the synthesis of novel $-lactam compounds and are closely related in structure to penicillanic acid sulphone, 2, a powerful @-lactamase inhibitor.'

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The synthesis of a d'carbapenem and two ,?-lactams possessing a Br-atom at the N-substituting center not involved in the lactam ring and bearing the carboxyl group is described. The ,?-lactams having this kind of Br-substitution are more susceptible to nucleophilic attack than those having a conjuga