Intermediates for beta-lactam antibiotics

Details Intermediates for beta-lactam antibiotics Intermediates for beta-lactam antibiotics

1988-04-22

1989-09-26

Rizzo, Nicholas S.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

540225, C07D26338, A61K 3142

Patent

active

048701696

ABSTRACT:
1-Benzyl(or substituted benzyl)-3.beta.-[4(S)-aryloxazolidin-2-one-3-yl]-4.beta.-(2-arylvinyl)azet idin-2-ones are provided via cycloaddition of a 4(S)-aryloxazolidin-2-one-3-ylacetyl halide and an imine formed with a benzylamine and a 3-arylacrolein, e.g. cinnamaldehyde. The azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-hydroxy-3-cephem-4-carboxylic acids and esters and to monocyclic .beta.-lactam antibiotics.

REFERENCES:
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patent: 4665171 (1987-05-01), Evans et al.
patent: 4772694 (1988-09-01), Cooper
Evans, D. A., et al., "Asymmetric Alkylation Reactions of Chiral Imide Enolates", J. Am. Chem. Soc., 1982, 104, 1737-1739.
Evans, D. A., et al., "Enantioselective Aldol Condensations. 2.", J. Am. Chem. Soc., 1981, 103, 2127-2129.
Close, W. J., "Anticonvulsant Drugs. IV. Some 2-Oxazolidones", J. Am. Chem. Soc., 1951, 73, 95.
Pirkle, W. H., et al., J. Org. Chem., vol. 48, No. 15 (1983), pp. 2520-2527.

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