Improved process for synthesizing carbapenem intermediates

C - Chemistry – Metallurgy – 07 – D

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C07D 477/18 (2006.01) C07D 477/04 (2006.01) C07F 7/10 (2006.01)

Patent

CA 2178935

This invention relates to the synthesis of a bicyclic ketoester compound of formula (I) obtained by cyclizing a diazo compound of formula (2) in the presence of a rhodium catalyst. By adding an effective amount of a Lewis acid to the cyclization reaction, the reaction selectively produces the 1-beta methyl isomer, and epimerization of the 1-beta methyl compound to the 1-alpha isomer is minimized.

L'invention concerne la synthèse d'un composé cétoester bicyclique de la formule (1) obtenu par cyclisation d'un composé diazo de la formule (2), en présence d'un catalyseur au rhodium. Si l'on ajoute une quantité efficace d'un acide de Lewis pour réaliser la réaction de cyclisation, ladite réaction produit, de façon sélective, l'isomère de 1-beta méthyle, et l'épimérisation du composé 1-beta méthyle en 1-alpha isomère est minimisée.

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