Synthesis of optically active cyclohexylphenylglycolic acid...

C - Chemistry – Metallurgy – 07 – C

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C07C 51/487 (2006.01) C07C 59/54 (2006.01) C07C 67/12 (2006.01) C07C 69/96 (2006.01) C07C 213/06 (2006.01) C07C 219/20 (2006.01)

Patent

CA 2347736

A process for the preparation of optically active cyclohexylglycolate esters is described. The process utilizes carboxylic acid activation to couple (R)- or (S)-cyclohexylphenylglycolic acid (CHPGA) with 4-N,N-diethylamino butynol or other propargyl alcohol derivatives. The preparation of the hydrochloride salt is also described. In addition, a resolution process employing tyrosine methyl ester enantiomers for preparing a single enantiomer of CHPGA from racemic CHPGA is disclosed.

L'invention concerne un procédé de préparation d'esters de cyclohexylphénylglycolate, actifs sur le plan optique. Ce procédé consiste à utiliser l'activation de l'acide carboxylique pour coupler l'acide (R)- ou (S)-cyclohexylphénylglycolique avec un 4-N,N-diéthylaminobutynol ou d'autres dérivés d'alcool propargylique. L'invention concerne également la préparation du sel d'hydrochlorure. En outre, elle concerne encore un procédé de résolution mettant en oeuvre des énantiomères de tyrosine méthylester, aux fins de préparation d'un seul énantiomère de CHPGA (acide cyclohexylphénylglycolique) à partir de CHPGA racémique.

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