Exploration of an efficient method for optical resolution of etodolac

Journal of the Chinese Chemical Society

Volumn 48, Issue 2, 2001, Pages 229-234

  Chou, Shan Yen ^a   Tseng, Chin Lu ^a   Chang, Lien Shange ^a  

^a DEVELOPMENT CENTER FOR BIOTECHNOLOGY   (Taiwan)

Author keywords

( ) Isopinocamphenol; Chiral etodolac; L Cinchonidine; Optical resolution

Indexed keywords

EID: 21244478305     PISSN: 00094536     EISSN: None     Source Type: Journal    
DOI: 10.1002/jccs.200100037     Document Type: Article

References (16)

1. Demerson, C. A.; Humber, L. G.; Dobson, T. A.; Jirkovsky, I. L. Ger. Offen. 1973, 2, 226, 340.
2. Vetter, G.; Placchi, M.; Joubert, L. Int. J. Clin. Pharmacol. Ther. Toxicol. 1982, 20, 240.
3. The active (+)-etodolac has been assigned an S absolute configuration on the basis of a crystallographic analysis of the (S)-(-)-borneol ester of (-)-etodolac, see: Humber, L. G.; Demerson, C. A.; Swaminathan, P.; Bird, P. H. J. Med. Chem. 1986, 29, 871.
4. Adger, B. M.; Dyer, U. C.; Woods, M.; Andrews, J. F. P.; Baker, H. F. PCT, Int. Appl. 1995, WO 9527713.
5. Abraham, N. A.; Demerson, C. A. U. S. Patent 1983, 4,501,899.
6. Demerson, C. A.; Humber, L. G. U. S. Patent, 1983, 4,515 961.
7. Abraham, N. A.; Demerson, C. A. U. S. Patent, 1983, 4,520,203.
8. Demerson, C. A.; Humber, L. G. U. S. Patent, 1984, 4,544,757.
9. Lane, C. F.; Daniels, J. J. Organic Synth. Coll. Vol. VI 1988, 719.
10. The ratio is estimated by a HPLC under conditions described in the general description of the experimental part of this article.
11. A known method was employed for preparation of compound 9, see: Demerson, C. A.; Humber, L. G. U. S. Patent 1986, 4,585,877.
12. Chou, S-Y.; Tseng, C.-L.; Chen, S.-F. Heterocycles 1999, 51, 1527.
13. 2O, r.t.), see: Strube, R. E. Organic Synth. Coll. Vol. IV 1962, 417.
14. Further work has shown that much shorter refluxing (1 h-0.5 h) have given a much higher purity of partially racemized etodolac (0.5-1 h), albeit a slightly lower extent of racemization (∼10-20%).
15. As shown by mass spectrum, the deuterio hydroxyl group of 16 was partially exchanged by protons during the periods of work-up and purification.
16. Baldwin, J. E. J. Chem. Soc., Chem. Commun. 1976, 734.