Process for the production of optically-active 4-amino-3-hydroxy

Details Process for the production of optically-active 4-amino-3-hydroxy Process for the production of optically-active 4-amino-3-hydroxy

1993-09-15

1994-10-04

Springer, David B.

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C07D207273

Patent

active

053528018

ABSTRACT:
Starting from 5-alkylidene or 5-benzylidenetetramic acid optically-active 4-amino-3-hydroxy-carboxylic acids are produced in the (rel-3R,4R) configuration, especially statine. The synthesis process includes the O-acylation of the tetramic acid to the corresponding 4-acyloxy-3-pyrrolin-2-one, a stereoselective hydrogenation to (rel-4R,5R)-4-acyloxy-5-alkyl or 5-benzylpyrrolidin-2-one and an enantioselective enzymatic hydrolysis of the (4R,5R)-enantiomer to 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 optionally introduction of an amino protective 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 producible according to the invention are the structural elements of enzyme inhibitors.

REFERENCES:
patent: 4876343 (1989-10-01), Hodges et al.
Katsuki et al., Bul. Chem. Soc. Japan, vol. 94, No. 11, (1976), pp. 3287 to 3290.
Altenbach, Nach. Aus Che., Tech. und Lab., vol. 36, No. 7, (1988), pp. 756 to 758.
H. Pielatzik et al., "Methoden Der Organischen Chemie", Houben-Weyl, 4th Ed., vol. E5, (1985), pp. 633 to 656.
G. Hesse, "Methoden Der Organischen Chemie", Houben-Weyl, 4th Ed., vol. VI/1d, (1978), pp. 108 to 115.

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