Method for preparing (s)-indoline-2-carboxylic acid and (s)-indoline-2-carboxylic acid methyl ester using hydrolytic enzyme
AssigneeSK Corporation
InventorsNahm Ryune Cho, Jong Ho Lim, Jong Keun Kim
Life of this patent
Estimating the term…
Abstract
Disclosed is a method for preparing (S)-indoline-2-carboxylic acid and (S)-indoline-2-carboxylic acid methyl ester using an inexpensive industrially available enzyme capable of assuring superior optical purity and yield. At this time, the hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7 and Acylase, whereby (S)-indoline-2-carboxylic acid and methyl ester thereof having an optical purity of at least 99% e.e. can be obtained through a simplified preparation process, thus generating economic benefits.
Claims14
A method for preparing (S)-indoline-2-carboxylic acid methyl ester by use of a hydrolytic enzyme, comprising the following steps:
- reacting racemic indoline-2-carboxylic acid with methanol and thionyl chloride, to give racemic indoline-2-carboxylic acid methyl ester;
- selectively hydrolyzing (R)-form of the racemic indoline-2-carboxylic acid methyl ester in a buffer solution by use of the hydrolytic enzyme to produce (S)-indoline-2-carboxylic acid methyl ester;
- and
- separating and recovering the (S)-indoline-2-carboxylic acid methyl ester, wherein said hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Novozym 243, Everlase, Esperase, Protease 7, and Acylase.
A method for preparing (S)-indoline-2-carboxylic acid by use of a hydrolytic enzyme, comprising the following steps:
- reacting racemic indoline-2-carboxylic acid with methanol and thionyl chloride, to give racemic indoline-2-carboxylic acid methyl ester;
- selectively hydrolyzing (R)-form of the racemic indoline-2-carboxylic acid methyl ester in a buffer solution by use of the hydrolytic enzyme to obtain an unhydrolyzed (S)-indoline-2-carboxylic acid methyl ester;
- separating and recovering the (S)-indoline-2-carboxylic acid methyl ester;
- and
- hydrolyzing the recovered (S)-indoline-2-carboxylic acid methyl ester in an alkali aqueous solution to produce (S)-indoline-2-carboxylic acid, followed by recovering the resulting (S)-indoline-2-carboxylic acid,
- wherein, said hydrolytic enzyme is selected from the group consisting of Savinase, Alcalase, Nvozym 243, Everlase, Esperase, Protease 7, and Acylase.
Dependencies are inferred from the claim text.