Process for producing bicyclocarboxylic acid derivative

Details Process for producing bicyclocarboxylic acid derivative Process for producing bicyclocarboxylic acid derivative

C - Chemistry, Metallurgy

07

C

C07C 51/377 (2006.01) C07C 62/24 (2006.01) C07C 67/327 (2006.01) C07C 69/757 (2006.01)

Patent

CA 2441127

A process for producing a 2-oxobicyclo[3.1.0]hex-3-ene-6-carboxylic acid derivative represented by the formula (I) (wherein R1 represents hydrogen, C1- 6 alkyl, C3-6 cycloalkyl, C1-6 alkyl substituted by C3-6 cycloalkyl, C1-6 alkyl substituted by optionally substituted phenyl, C1-6 alkyl substituted by C1-6 alkoxy, C1-6 hydroxyalkyl, C1-6 alkyl substituted by C1-6 alkylthio, C1-6 mercaptoalkyl, or optionally substituted phenyl), characterized by reacting a 4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylic acid derivative represented by the formula (II) (wherein R1 is the same as defined above; and R2 represents hydrogen or a hydroxyl-protecting group) in the presence of an acid or base. Also provided is a process for producing a compound useful in the efficient synthesis of a 2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylic acid derivative.

L'invention porte sur un procédé de production d'un dérivé d'acide 2-oxobicyclo[3.1.0]hex-3-ène-6-carboxylique représenté par la formule (I) (dans laquelle R?1¿ représente un hydrogène, alkyle C¿1?-C¿6?, cycloalkyle C¿3?-C¿6?, alkyle C¿1?-C¿6? substitué par cycloalkyle C¿3?-C¿6?, alkyle C¿1?-C¿6? substitué par un phényle éventuellement substitué, alkyle C¿1?-C¿6? substitué par alcoxy C¿1?-C¿6?, hydroxyalkyle C¿1?-C¿6?, alkyle C¿1?-C¿6? substitué par alkylthio C¿1?-C¿6?, mercaptoalkyle C¿1?-C¿6? ou phényle éventuellement substitué), caractérisée en ce qu'elle met en réaction un dérivé d'acide 4-hydroxy-2-oxobicyclo[3.1.0]hexane-6-carboxylique représenté par la formule (II) (dans laquelle R?1¿ est identique à celui défini ci-dessus; et R?2¿ représente un hydrogène ou un groupe de protection hydroxyle) en présence d'un acide ou d'une base. Fait aussi l'objet de cette invention un procédé de production d'un composé utile dans la synthèse efficace d'un dérivé d'acide 2-amino-3-fluorobicyclo[3.1.0]hexane-2,6-dicarboxylique.

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