(6s)-5,6,7,8-tetrahydrofolic acid production process

Details (6s)-5,6,7,8-tetrahydrofolic acid production process (6s)-5,6,7,8-tetrahydrofolic acid production process

C - Chemistry, Metallurgy

07

D

C07D 475/04 (2006.01)

Patent

CA 2474317

New process for the production of (6S)-5,6,7,8-tetrahydrofolic acid or derivatives thereof starting from the corresponding (6S, 6R) racemic mixture. The procedure comprises in the steps of adding an organic acid to a non- alkaline suspension of (6S,6R)-5,6,7,8-tetrahydrofolic acid, up to a pH value in the range of 1 to 3; heating the suspension from 30~ to 80~C; cooling the suspension from 20~ to 60~C, with selective crystallization of the (6S)- isomer. The procedure gives the (6S)-isomer in high yields and with a high degree of stereoselectivity. It follows that the synthetic access to a large number of pharmacologically active stereoisomers of folic acid is simpler and more effective.

L'invention concerne un nouveau procédé de production d'acide (6S)-5,6,7,8-tétrahydrofolique ou de dérivés dudit acide à partir du mélange racémique correspondant (6S, 6R). Ce procédé consiste à ajouter un acide organique dans une suspension non alcaline d'acide (6S,6R)-5,6,7,8-tétrahydrofolique jusqu'à l'obtention d'une valeur de pH comprise entre 1 et 3, à chauffer cette suspension à une température comprise entre 30· et 80 ·C, puis à refroidir la suspension de 20· à 60 ·C, avec une cristallisation sélective du (6S)-isomère. Ce procédé permet de produire le (6S)-isomère avec un rendement élevé et une haute stéréosélectivité, d'où un accès synthétique plus simple et plus efficace à un grand nombre de stéréoisomères d'acide folique pharmacologiquement actifs.

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