Process and intermediates for .beta.-lactam antibiotics

Details Process and intermediates for .beta.-lactam antibiotics Process and intermediates for .beta.-lactam antibiotics

1985-07-17

1987-05-12

Berch, Mark L.

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

Organic compounds

Unsubstituted hydrocarbyl chain between the ring and the -c-...

540363, 548112, 548229, 548232, 560 29, C07D20508, C07D41304, C07D26324, C07F 965

Patent

active

046651713

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: 4166816 (1979-09-01), Gleason
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patent: 4226866 (1980-10-01), Christensen et al.
patent: 4472576 (1984-09-01), Wakazawa et al.
N. Hatanaka et al., Tetrahedron Letters, vol. 24, No. 44, pp. 4837-4838, 1983.
Guthikonda, R. N., et al., J. Am. Chem. Soc., 96, 7584 (1974).
Firestone, R. A., et al., J. Med. Chem., 20, No. 4, 551 (1977).

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