Process for the production of optically-active...

Details Process for the production of optically-active... Process for the production of optically-active...

C - Chemistry, Metallurgy

12

P

C12P 13/00 (2006.01) C07D 207/273 (2006.01) C12P 41/00 (2006.01)

Patent

CA 2076580

ABSTRACT OF THE DISCLOSURE A process is disclosed for the production of optically-active 4-amino-3-hydroxy-carboxylic acids in the (rel-3R,4R) configuration, especially statine, starting from 5-alkylidene or 5-benzylidenetetramic acid. The synthesis process includes the 0-acylation of the tetramic acid to form the corresponding 4-acyloxy-3-pyrrolin-2-one, a stereoselective hydrogenation to produce (rel-4R,5R)-4- acyloxy-5-alkyl or 5-benzylpyrrolidin-2-one and an enantioselective enzymatic hydrolysis of the (4R,5R)- enantiomer to form the corresponding 4-hydroxypyrrolidin-2- one. The nonhydrolyzed enantiomer is separated and converted into the target compound with (3S,4S) configuration by hydrolytic cleavage of the lactam ring and the ester function and optional introduction of an amino protecting group. Analogously, the (3R,4R)-enantiomer can be obtained from the 4-hydroxypyrrolidin-2-one from the enzymatic hydrolysis. The 4-amino-3-hydroxycarboxylic acids produced by the process of the invention are the structural elements of enzyme inhibitors.

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