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Process for preparing optically active indoline-2-carboxylic acid

  • US 4,898,822 A
  • Filed: 03/31/1986
  • Issued: 02/06/1990
  • Est. Priority Date: 04/01/1985
  • Status: Expired due to Fees
First Claim
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1. A process for preparing an (R)-indoline-2-carboxylic acid having the formula [(R)-II]:

  • ##STR12## which comprises subjecting a racemic ester of an (R,S)-indoline-2-carboxylic acid having the formula [(R,S)-I)];

    ##STR13## wherein R is an alkyl or alkenyl group having 1 to 10 carbon atoms;

    an alkyl or alkenyl group having 1 to 10 carbon atoms substituted with either hydroxyl group or a halogen atom, or simultaneously substituted with both hydroxyl group and a halogen atom;

    or a substituted or unsubstituted aromatic hydrocarbon group, to the action of an enzyme selected from the group consisting of Protease Amano P, Bioplase AL 15, Actinase E, Pancreatic digesting enzyme TA, Steapsin and Lipase L 3216, or a microorganism selected from the group consisting of Aspergillus melleus IFO 4420, Bacillus subtilis IFO 3018, Streptomyces griseus IFO 8358, Saccharomyces cerevisiae HUT 7018, Trichosporon cutaneum IFO 1200, Aeromonas hydrophila IFO 3820, Arthrobacter paraffineus ATCC 21317, Arthrobacter nicotianae IFO 14234, Acidiphilium cryptum IFO 14242, Brevibacterium protophormiae IFO 12128, Corynebacterium paurometabolum IFO 12160 and Pseudomonas oxalacticus IFO 13593, or a stereoselective esterase from any of these microorganisms, to asymmetrically hydrolyze the racemic ester [(R,S)-I] into optically active (R)-indoline-2-carboxylic acid [(R)-II] and an ester of (S-indoline-2-carboxylic acid having the formula [(S)-1] ##STR14## wherein R is as above, and then isolating the optically active (R)-indoline-2-carboxylic acid [(R)-II].

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