Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1986-07-10
1988-03-29
Berch, Mark L.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
548547, 560171, C07D20508, C07D40514, C07D40304, C07D40914
Patent
active
047344989
ABSTRACT:
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.
REFERENCES:
Ikota, Chem. Abs. 102, 78623, (1984).
M. Hatanaka et al., Tetrahedron Letters, vol. 24, No. 44, pp. 4837-4838, 1983.
N. Ikota and A. Hanaka, Heterocycles, vol. 22, No. 10, 1984.
Berch Mark L.
Eli Lilly and Company
Scanlon William B.
Whitaker Leroy
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