Azetidinone intermediates to carbacephalosporins and process

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

1995-04-25

1997-07-08

Berch, Mark L.

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

Organic compounds

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

C07D205085, C07D46300

Patent

active

056462751

ABSTRACT:
7.beta.-Amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are provided via cyclization of compounds of Formula IIA below. ##STR1## The 7.beta.-Amino-3-hydroxy-l-carba(1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates in the synthesis of .beta.-lactam antibiotics.

REFERENCES:
patent: 4665171 (1987-05-01), Evans et al.
Jackson, et al., Tetrahedron Letters, vol. 31, No. 44, pp. 6317-6320, 1990, "Synthesis of Carbacephem Antibiotics: Synthesis via Dieckmann Reaction Using Phenyl Esters to Direct the Regioselectivity of the Cyclization."
Hatanaka et al., Tetrahedron Letters, vol. 24, No. 44, pp. 4837-4838, 1983, "A Simple Synthesis of (+/-)-1-Carbacephem Derivatives."
Campaigne, et al., J. Het. Chem., 14, 497, 1976, Chemistry Laboratories of Indiana University, Bloomington Indiana 47401, Jan. 28, 1976, "Synthesis of Some 5-Aryl-2.2'-dipyrromethenes as Analogs of Prodigiosin (1)".
Mauger et al., J. Org. Chemistry, vo. 42, No. 6, 1977, "Synthesis and Stereochemistry of 3-Hydroxy-5-methylproline, a New Naturally Occuring Imino Acid".
Blake, et al., JACS, 86, 5293 (1964), "Pyrrolidinones by Intramolecular Condensation".

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