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filingDate 1992-08-18-04:00^^<http://www.w3.org/2001/XMLSchema#date>
grantDate 1996-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_0206cca2d66592c6e224cd8d4075379b
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_97004a0b47eeabc61de0fe1674a45353
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publicationDate 1996-02-28-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0529483-B1
titleOfInvention Process for the preparation of optically active 4-amino-3-hydroxycarboxylic acids
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.
priorityDate 1991-08-22-04:00^^<http://www.w3.org/2001/XMLSchema#date>
type http://data.epo.org/linked-data/def/patent/Publication

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