3.beta.-succinimidoazetidinones as chiral intermediates
AssigneeEli Lilly and Company
InventorRobin D. G. Cooper
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AssigneeEli Lilly and Company
InventorRobin D. G. Cooper
Estimating the term…
3.beta.-Substituted succinimido)azetidinones represented by the formula ##STR1## wherein R and R.sub.1 are e.g. C.sub.1 -C.sub.5 alkanoyloxy, benzoyloxy, substituted benzoyloxy, or benzyloxy, or one of R and R.sub.1 is hydrogen and the other is as defined above; R.sub.2 is C.sub.1 -C.sub.4 alkoxycarbonyl or an arylvinyl group e.g. styrryl or 2-furylvinyl; and R.sub.3 is e.g. protected-carboxymethyl, or an NH protecting group; are provided via stereoselective cycloaddition of imines with chiral auxiliary 3,4-disubstituted succinimidoacetyl chlorides. The chiral auxiliary e.g., 3S,4S-dibenzoyloxy-and 3S,4S-diacetoxysuccinimidoacetyl chloride, is obtained from tartaric acid via anhydride and imide formation with retention of chirality. The chiral azetidinones obtained are useful intermediates to .beta.-lactam antibacterial compounds.
The compound of the formula ##STR18## wherein R and R.sub.1 are C.sub.1-C.sub.5 alkanoyloxy, benzoyloxy, a mono- or di-substituted benzoyloxy group substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano, nitro, amino, or C.sub.1 -C.sub.4 alkoxy carbonyl, benzyloxy, diphenylmethoxy, or triphenylmethoxy;
The compound of the formula ##STR22## wherein R and R.sub.1 are C.sub.1 -C.sub.5 alkanoyloxy, benzoyloxy, a substituted benzoyloxy group substituted by C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 alkoxy, halogen, cyano, nitro, amino, or C.sub.1 -C.sub.4 alkoxy carbonyl, benzyloxy, diphenylethoxy or triphenylmethoxy;
Dependencies are inferred from the claim text.