Azetidinone intermediates to carbacephalosporins and process

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

C - Chemistry, Metallurgy

07

D

260/271, 260/336

C07D 205/085 (2006.01) A61K 31/395 (2006.01) C07D 471/04 (2006.01) C07D 477/00 (2006.01) C07D 501/46 (2006.01)

Patent

CA 1336977

7.beta.-amino-3-hydroxy-1-carba(1-dethia)-3-cephem-4- carboxylic acid esters of Formula (I): Image (I) wherein R1 is C1-C6 alkyl; a phenyl group Image wherein a and a' independently are hydrogen, C1-C4 alkyl, C1-C4 alkoxy or halogen; a group represented by the formula Image wherein Z is O or S, m is 0 or 1, and a and a' have the same meanings as defined above; or R1 is R1'O wherein R1' represents C1-C4 alkyl, C5-C7 cycloalkyl, benzyl, nitrobenzyl, methoxybenzyl, or halobenzyl; and R2 is a carboxy-protecting group, are prepared by cyclization of cis-3-(substituted amino)-1-(2-substituted 2- oxoethyl)-4-azetidin-2-one propanoic acid esters of Formula (II): Image (II) wherein R1 and R2 are as defined above and R3 is a leaving roup, employing a non-nucleophilic strong base. The 7.beta.-amino-3- hydroxy-1-carba(1-dethia)-3-cephem-4-carboxylic acid esters are useful chiral intermediates to .beta.-lactam antibiotics.

614237

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