Azetidinone intermediates to carbacephalosporins and process

Details Azetidinone intermediates to carbacephalosporins and process Azetidinone intermediates to carbacephalosporins and process

1995-06-05

1997-06-10

Berch, Mark L.

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

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D46300, C07D205085, C07B 3710

Patent

active

056376928

ABSTRACT:
7.beta.-Amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are provided via cyclization of cis-3-(substituted amino)-1-(2-substituted 2-oxoethyl)-4-substituted azetidinones. The 7.beta.-amino-3-hydroxy-1-carba (1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates to .beta.-lactam antibiotics.

REFERENCES:
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Hatanaka et al., Tetrahedron Letters, 24(44), pp. 4837-4838 (1983), "A Simple Synthesis of (+/-)-1-Carbacephem Derivatives."
Campaigne, et al., J. Het. Chem., 14, 497-503, 1976, "Synthesis of Some 5-Aryl-2.2'-dipyrromethenes as Analogs of Prodigiosin (1)".
Mauger et al., J. Org. Chemistry, 42(6), 1000-1005 (1977), "Synthesis and Stereochemistry of 3-Hydroxy-5-methylproline, a New Naturally Occurring Imino Acid".
Blake, et al., JACS, 86, 5293-5299 (1964), "Pyrrolidinones by Intramolecular Condensation".
Bonjoch et al., Tetrahedron, 40(13), pp.2505-2511 (1984), "Synthesis of 2,5-Piperidinediones. Regioselectivity in the Dieckmann Cyclization.sup.1. "
Nagao et al., Chemistry Letters, 1861-1864 (1987), "A New Finding in the Dieckmann Type Annulation of a Chiral Half-Thiol Diester Having Latent .sigma.-Symmetry."

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