US 12,188,066 B2
Method for resolving optical isomer by using supercritical fluid extraction technology
Man Kit Lau, Guang An (CN); Jinhuan Su, Guang An (CN); Ansen Chiew, Guang An (CN); Yan Chen, Guang An (CN); and Congming Zeng, Guang An (CN)
Assigned to Guang An Mojia Biotechnology Co., Ltd., Guang An (CN)
Appl. No. 17/606,448
Filed by Guang An Mojia Biotechnology Co., Ltd., Guang An (CN)
PCT Filed Apr. 23, 2020, PCT No. PCT/CN2020/086420
§ 371(c)(1), (2) Date Oct. 25, 2021,
PCT Pub. No. WO2020/216295, PCT Pub. Date Oct. 29, 2020.
Claims priority of application No. 201910343769.6 (CN), filed on Apr. 26, 2019.
Prior Publication US 2022/0195471 A1, Jun. 23, 2022
Int. Cl. C12P 17/04 (2006.01); B01D 11/04 (2006.01); C07D 307/33 (2006.01)
CPC C12P 17/04 (2013.01) [B01D 11/0403 (2013.01); C07D 307/33 (2013.01); C07B 2200/07 (2013.01); C07B 2200/13 (2013.01)] 11 Claims
 
1. A method for resolving an optical isomer from a racemate by using a supercritical fluid extraction technique, comprising:
a) reacting the racemate in the presence of a catalyst to form a mixture comprising a first form of a first optical isomer and a second form of a second optical isomer;
b) performing an extraction with supercritical fluid on the mixture to allow the first form of the first optical isomer and the second form of the second optical isomer to be separated; and
c) collecting the separated first form of the first optical isomer, and/or collecting the separated second form of the second optical isomer,
wherein
the catalyst is an ester hydrolase and/or a lactamase;
(1) the racemate is DL-pantolactone, the first form of the first optical isomer is D-pantoic acid, and the second form of the second optical isomer is L-pantolactone;
(2) the racemate is methyl 3-cyclohexene-1-carboxylate, the first form of the first optical isomer is (R)-3-cyclohexene-1-carboxylic acid, and the second form of the second optical isomer is(S)-methyl 3-cyclohexene-1-carboxylate;
(3) the racemate is α-hydroxy-γ-butyrolactone, the first form of the first optical isomer is (R)-α-hydroxy-γ-butyric acid, and the second form of the second optical isomer is(S)-α-hydroxy-γ-butyrolactone;
(4) the racemate is β-hydroxy-γ-butyrolactone, the first form of the first optical isomer is (R)-β-hydroxy-γ-butyric acid, and the second form of the second optical isomer is(S)-β-hydroxy-γ-butyrolactone; or
(5) the racemate is α-acetyl-γ-butyrolactone, the first form of the first optical isomer is (R)-α-acetyl-γ-butyric acid, and the second form of the second optical isomer is(S)-α-acetyl-γ-butyrolactone.