Racemization process for optically active carboxylic acids...

C - Chemistry – Metallurgy – 07 – C

Patent

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C07C 59/68 (2006.01) C07C 51/42 (2006.01) C07C 51/487 (2006.01) C07C 55/00 (2006.01) C07C 57/30 (2006.01) C07C 57/58 (2006.01) C07C 59/84 (2006.01) C07C 67/333 (2006.01) C07C 67/48 (2006.01) C07C 69/612 (2006.01) C07C 69/736 (2006.01) C07C 69/738 (2006.01) C07C 319/26 (2006.01) C07D 207/20 (2006.01) C07D 333/24 (2006.01)

Patent

CA 2258085

Optically active carboxylic acids, salts or esters, such as the profen-type compounds, are racemized in the presence by nitrogenous bases such as methylbenzyl-amine by heating an aqueous solution of such optically active compounds at a temperature of from 80 ~C to 200 ~C in the presence of a catalytically effective amount of an alkali metal hydroxide. The process not only enables conversion of inactive or undesirable enantiomers of compounds such as Naproxen or Ibuprofen into a usable, desirable enatiomers in an efficient and economical manner, but avoids conversion of the nitrogenous base into amide. Thus the deleterious consequences of amide formation are avoided.

Cette invention concerne un procédé de racémisation d'acides carboxyliques optiquement actifs, de sels ou d'esters de ces acides, tels que des composés de type profène, en présence de bases azotées du type méthylbenzyl-amine. Ledit procédé consiste à chauffer une solution aqueuse de ces composés optiquement actifs à une température comprise entre 80 ·C et 200 ·C en présence d'une quantité catalytiquement active d'un hydroxyde de métal alcalin. Ce procédé permet non seulement la conversion efficace et économique d'énantiomères inactifs ou indésirables de composés tels que le Naproxène et l'Ibuprofène en énantiomères utiles et désirables, mais il permet également d'éviter la conversion de la base azotée en amide. On évite ainsi les effets nocifs liés à la formation d'amide.

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