Process for the synthesis of azetidinones

Details Process for the synthesis of azetidinones Process for the synthesis of azetidinones

C - Chemistry, Metallurgy

07

D

C07D 205/08 (2006.01)

Patent

CA 2591564

A process is provided for preparing azetidinones useful as intermediates in the synthesis of penems and as hypoc-holesterolemic agents, comprising reacting a .beta.-(substituted- amino)amide, a .beta.-(substituted-amino)acid ester, or a .beta.-(substituted--amino)thiolcarbonic acid ester with a silylating agent and a cyclizing agent selected from the group consisting of alkali metal car-boxylates, quaternary ammonium carboxylates, quaternary ammonium hydroxides, quaternary ammonium alkoxides, quaternary ammonium aryloxides and hydrates thereof, or the reaction product of: (i) at least one quaternary ammonium halide and at least one alkali metal carboxylate; or (ii) at least one quaternary ammonium chloride, quaternary ammonium bromide, or quaternary ammo-nium iodide and at least one alkali metal fluoride, wherein a quaternary ammonium moiety of the cyclizing agent is unsubstituted or substituted by one to four groups independently selected from the group consisting of alkyl, arylalkyl and arylalkyl-alkyl.

L'invention porte sur un procédé permettant de préparer des azétidinones utilisées comme intermédiaires dans la synthèse de penems et comme agents hypocholestérolémiants, qui consiste à faire réagir un amide amino-substitué en ß, un ester d'acide amino-substitué en ß, ou un ester d'acide thiolcarbonique amino-substitué en ß avec un agent de silylation et un agent de cyclisation choisi dans le groupe composé des carboxylates de métaux alcalins, des carboxylates d'ammonium quaternaire, des hydroxides d'ammonium quaternaire, des alcoxides d'ammonium quaternaire, des aryloxides d'ammonium quaternaire et des hydrates de ces derniers, ou le produit réactionnel de: (i) au moins un halogénure d'ammonium quaternaire et au moins un carboxylate de métal alcalin; ou (ii) au moins un chlorure d'ammonium quaternaire, un bromure d'ammonium quaternaire ou un iodure d'ammonium quaternaire et au moins un fluorure de métal alcalin, un fragment ammonium quaternaire de l'agent de cyclisation étant non substitué ou substitué par un à quatre groupes choisis indépendamment dans le groupe composé de l'alkyle, de l'arylalkyle et de l'arylalkyle-alkyle.

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