C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
260/304, 260/311
C07D 263/02 (2006.01) C07D 413/04 (2006.01) C07D 413/14 (2006.01)
Patent
CA 1329210
ABSTRACT OF THE DISCLOSURE The present invention provides 1-benzyl (or substituted benzyl)-3.beta.-[4(S)-aryl-oxazolidin-2-one-3-yl]- 4.beta.-(2-arylvinyl)azetidin-2-ones represented by the formula (1): Image 1 wherein Ar is phenyl, C1-C4 alkylphenyl, halophenyl, C1- C4 alkoxyphenyl, naphthyl, thienyl, furyl, benzothienyl, or benzofuryl; R is phenyl, C1-C4 alkylphenyl, C1-C4 alkoxyphenyl, or halophenyl; Y is -CH=CH-, or -CH2-CH2-; and R' is phenyl, C1-C4 alkoxyphenyl halophenyl, furyl or naphthyl. These compounds of Formula (1) 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, eg. cinnamaldehyde. The above azetidinones are useful chiral intermediates in an asymmetric synthesis of 1-carba(1-dethia)-3-cephem-4- carboxylic acids and esters (which have utility as antibiotics), and are also useful as intermediates in the synthesis of monocyclic .beta.-lactam antibiotics.
616413
Evans David Albert
Sjogren Eric Brian
Gowling Lafleur Henderson Llp
President And Fellows Of Harvard College
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