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classificationCPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentcpc/C07D209-42
classificationIPCInventive http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07B57-00
http://rdf.ncbi.nlm.nih.gov/pubchem/patentipc/C07D209-42
filingDate 1999-02-10-04:00^^<http://www.w3.org/2001/XMLSchema#date>
inventor http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_b934e483f16a3ca940e2acee80afcb73
http://rdf.ncbi.nlm.nih.gov/pubchem/patentinventor/MD5_d6a5b2ba150e038a9eaddc4c8bd9c661
publicationDate 1999-08-25-04:00^^<http://www.w3.org/2001/XMLSchema#date>
publicationNumber EP-0937714-A1
titleOfInvention Process for the preparation of an optically active indoline-2-carboxylic acid or derivative thereof
abstract Process for the preparation of an opticallynactive N-acyl-indoline-2-carboxylic acid in which anmixture of enantiomers of N-acyl-indoline-2-carboxylicnacid is contacted with an optically active resolvingnagent and the optically active N-acyl-indoline-2-carboxylicnacid is liberated from the resultingndiastereomeric salt, as resolving agent use being madenof a compound of formula 1, where R 1 represents annalkyl group and R 2 a (hetero) aryl group or where R 1 andnR 2 together with the C atoms to which they are boundnform a cycloalkyl group with 5-8 C atoms, fused with an(hetero) aryl group. Preferably, a mixture ofnenantiomers of an N-acyl-indoline-2-carboxylic acid isnprepared in a process comprising the steps of Fischernindole cyclization of a 2-phenylhydrazone propionicnacid or a derivative thereof in the presence of an acidncatalyst, if necessary hydrolysis of the derivative tonthe corresponding acid, acylation at the N-position andnreduction of the indole compound to the correspondingnindoline compound, after which the resulting N-acyl-indoline-2-carboxylicnacid is subjected to thenresolution. The 2-phenylhydrazonopropionic acid or anderivative thereof is preferably obtained fromnphenylhydrazine and pyruvic acid or the correspondingnderivative thereof.
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