Process for manufacturing a glutamic acid derivative and a...

Details Process for manufacturing a glutamic acid derivative and a... Process for manufacturing a glutamic acid derivative and a...

C - Chemistry, Metallurgy

07

F

C07F 7/18 (2006.01) C07C 227/22 (2006.01) C07D 207/28 (2006.01) C07D 209/20 (2006.01) C07D 403/06 (2006.01) C07C 229/24 (2006.01)

Patent

CA 2512752

A process for producing a glutamic acid derivative represented by monatin, which comprises alkylating a 4-(protected hydroxy)pyroglutamic acid derivative with an alkylating agent to obtain a 4-(protected hydroxy)-4-alkylgultamic acid derivative and subjecting it to hydrolysis and protective-group elimination. The 4-(protected hydroxy)pyroglutamic acid derivative can be easily produced from hydroxyproline. The 4-(protected hydroxy)pyroglutamic acid derivative is selectively and stereoselectively alkylated in the 4- position and, after the alkylation, can be easily converted to a glutamic acid derivative. It can hence be advantageously used especially for efficiently producing monatin having a high optical purity.

L'invention concerne un procédé permettant de produire un dérivé d'acide glutamique représenté par la monatine. Ledit procédé consiste à alkyler un dérivé d'acide 4-(hydroxy protégé)pyroglutamique avec un agent d'alkylation afin d'obtenir un dérivé d'acide 4-(hydroxy protégé)-4-alkylglutamique, et à le soumettre à une hydrolyse et à une élimination de groupe protecteur. Le dérivé d'acide 4-(hydroxy protégé)pyroglutamique peut être facilement produit à partir de l'hydroxyyproline. Ledit dérivé d'acide 4-(hydroxy protégé)pyroglutamique est sélectivement et stéréosélectivement alkylé en position 4 et peut, après l'alkylation, être facilement converti en un dérivé d'acide glutamique. Il peut être avantageusement utilisé pour produire efficacement de la monatine à pureté optique élevée.

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