C - Chemistry – Metallurgy – 07 – D
Patent
C - Chemistry, Metallurgy
07
D
C07D 209/42 (2006.01)
Patent
CA 2488324
Processes for: a) separating the enantiomers of indoline-2-carboxylic acid of formula 1 Image comprising of (i) combining the (R, S)-indoline-2-carboxylic acid with (1S)- or (1R)-10- camphorsulfonic acid as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-indoline-2-carboxylic acid with optically pure (1S)- or (1R)-10-camphorsulfonic acid; (ii) regenerating the (S)- or (R)-indoline-2-carboxylic acid from the crystallized diastereomeric salt by using a suitable base or basic ion-exchange resin; and b) for the optical resolution of N-acetyl-indoline-2-carboxylic acid of formula 2 Image comprising of: (i) combining the (R, S)-N-acetyl-indoline-2-carboxylic acid with (S)- or (R)- phenylglycinol as the resolving agent in a resolution solvent and crystallizing from the said mixture the diastereomeric salt of (S)- or (R)-N-acetyl-indoline-2- carboxylic acid with optically pure phenylglycinol; (ii) regenerating the (S)- or (R)-N-acetyl-indoline-2-carboxylic acid from the crystallized salt by using a suitable acid or acidic ion-exchange resin. The non-selected enantiomer may then be racemized and the process (a) or (b) repeated thus to obtain substantial conversion of the material to one enantiomer.
Raheem Mohammed Abdul
Wang Zhi-Xian
Weeratunga Gamini
Apotex Pharmachem Inc.
Mckinnon Graham J.k.
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