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

1992-08-20

1994-02-15

Robinson, Douglas W.

Chemistry: molecular biology and microbiology

Process of utilizing an enzyme or micro-organism to destroy...

Resolution of optical isomers or purification of organic...

435106, C12P 1304

Patent

active

052866505

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:
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/ld, (1978), pp. 108 to 115.

Affiliated with

Also associated with

Rating

Process for the production of optically-active 4-amino-3-hydroxy does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process for the production of optically-active 4-amino-3-hydroxy, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for the production of optically-active 4-amino-3-hydroxy will most certainly appreciate the feedback.

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-1206366