Process for preparing optically active 2-amino-w-oxoalkanoic...

Details Process for preparing optically active 2-amino-w-oxoalkanoic... Process for preparing optically active 2-amino-w-oxoalkanoic...

C - Chemistry, Metallurgy

07

D

C07D 317/30 (2006.01) A61K 31/16 (2006.01) A61K 31/19 (2006.01) A61K 31/275 (2006.01) A61K 31/335 (2006.01) C07C 229/22 (2006.01) C07C 231/06 (2006.01) C07C 237/04 (2006.01) C07C 253/00 (2006.01) C07C 255/24 (2006.01) C07C 255/26 (2006.01) C07D 317/28 (2006.01) C07D 319/06 (2006.01) C12P 13/04 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2247952

Process for preparing an (S)-2-amino-.omega.-oxoalkanoic acid derivative in which the corresponding aldehyde is converted into the corresponding acetal-protected aldehyde, the acetal-protected aldehyde is converted into the corresponding aminonitrile, the aminonitrile is converted into the corresponding amino acid amide, the amino acid amide is subjected to an enzymatic, enantioselective hydrolysis in which the R enantiomer of the amino acid amide remains and the S enantiomer is converted into the S amino acid, and the S amino acid is isolated. Preferably, the reaction mixture obtained after the conversion of the aminonitrile into the amino acid amide is treated with a benzaldehyde, upon which the Schiff base of the amino acid amide is formed, the Schiff base is separated and is converted into the free amino acid amide.

Divulgation d'un procédé de préparation d'un dérivé d'un acide (S)-2-amino-.oméga.-oxoalcanoïque, au cours duquel on réalise les étapes suivantes : l'aldéhyde correspondant est converti en un aldéhyde correspondant à fonction acétal protégée; cet aldéhyde à fonction acétal protégée est converti en un aminonitrile correspondant; cet aminonitrile est alors converti en un amino-acétamide correspondant; et cet amino-acétamide est à son tour soumis à une hydrolyse enzymatique et énantiosélective, au cours de laquelle l'énantiomère R de l'amino-acétamide subsiste alors que l'énantiomère S est converti en acide aminé S, ce dernier étant alors isolé. De préférence, le mélange réactionnel obtenu après la conversion de l'aminonitrile en amino-acétamide est traité avec un benzaldéhyde, permettant d'obtenir une base de Schiff de l'amino-acétamide, qui est séparée et convertie en amino-acétamide libre.

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