Preparation of optically active aliphatic carboxylic acids

Details Preparation of optically active aliphatic carboxylic acids Preparation of optically active aliphatic carboxylic acids

C - Chemistry, Metallurgy

07

C

C07C 215/10 (2006.01) C07B 57/00 (2006.01) C07C 51/487 (2006.01) C07C 57/30 (2006.01) C07C 57/58 (2006.01) C07C 59/64 (2006.01) C07C 67/60 (2006.01) C07C 69/612 (2006.01) C07C 69/65 (2006.01) C07C 213/10 (2006.01)

Patent

CA 2211265

A process for the separation of a racemic mixture of certain aliphatic carboxylic acids or esters thereof is disclosed. The process comprises: (i) forming a diastereomeric salt by reaction comprising said racemic mixture of a C1 to C6 linear or branched aliphatic carboxylic acid and an amount of an N- alkyl-D-glucamine that is sufficient to react with one of the enantiomers of the racemic mixture; (ii) precipitating from the reaction solution formed in step (i) the diastereomeric salt; (iii) separating said precipitated diastereomeric salt; (iv) decomposing the salt into its enantiomeric component and its organic base component; and (v) isolating a substantially pure enantiomer from said decomposed salt.

L'invention concerne un procédé pour la séparation à partir d'un mélange racénique de certains acides carboxyliques aliphatiques ou de leurs esters. Le procédé comprend les étapes suivantes: (i) formation d'un sel diasestéréo-isomère par réaction du mélange racénique d'un acide carboxylique aliphatique C¿1? à C¿6? linéaire ou ramifié et d'un quantité de N-alkyl-D-glutamine suffisante pour réagir avec l'un des énantiomères dudit mélange; (ii) précipitation du sel diasestéréoisomérique obtenu à partir de la solution réactive décrite en (i); (iii) séparation du sel précipité en question; (iv) décomposition du sel en sa composante énantiomère et sa composante de base organique; et, enfin (v) isolation d'un énantiomère sensiblement pur à partir dudit sel décomposé.

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