Process for the preparation of 4-acyloxy-2-azetidinone...

C - Chemistry – Metallurgy – 07 – D

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260/335.5

C07D 205/08 (2006.01) C07F 7/10 (2006.01) C07F 7/18 (2006.01)

Patent

CA 2000565

Disclosed is a process for preparing a 4-acyloxy- 2-azetidinone derivatives of the following formula: Image wherein OR is a protected hydroxy group and Y is an acyl group, which comprises reacting a 2-azetidinone derivative of the following formula: Image wherein OR has the same meaning as defined above and X is an alkyl group or an aromatic group,and a copper oxide or copper salt of an organic carboxylic acid,in the presence of an organic carboxylic acid or a salt of an organic carboxylic acid as an acyl group source. The process is an effective route for producing 3-[1'-(R)-hydroxy- ethyl]-4-acyloxyazetidinone, an intermediate for synthesizing penems or carbapenems, without using a mercury salt which can cause an environmental hazard.

L'invention porte sur une méthode pour préparer des dérivés de 4-acyloxy-2-azétidinone de formule Image , où OR est un groupe hydroxy protégé et Y un groupe acyle. La méthode consiste à faire réagir un dérivé de 2-azétidinone de formule Image - où OR a la même signification que ci-dessus, X étant un groupe alkyle ou un groupe aromatique - avec un oxyde ou un sel de cuivre d'un acide carboxylique organique, en présence d'un acide carboxylique organique ou d'un sel d'un acide carboxylique organique comme source de groupe acyle. La méthode permet de produire efficacement la 3-¢1'-(R)-hydroxy-éthyl!-4-acyloxyazétidinone, un intermédiaire pour la synthèse de pénèmes ou de carbapénèmes, sans utilisation de sel de mercure, qui représente une menace pour l'environnement.

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