Anhydrides as acylating agents in the enzymatic resolution of an intermediate of (-)-Paroxetine

Journal of Organic Chemistry

Volumn 68, Issue 8, 2003, Pages 3333-3336

  De Gonzalo, Gonzalo ^a   Brieva, Rosario ^a   Sánchez, Víctor M ^a,b   Bayod, Miguel ^a,b   Gotor, Vicente ^a  

^a UNIVERSITY OF OVIEDO   (Spain)

^b Astur Pharma S A P Indust S ^*  (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ACYLATION; AROMATIC COMPOUNDS; CATALYST SELECTIVITY; ENZYME KINETICS; ESTERIFICATION; ISOMERS; ORGANIC SOLVENTS; STEREOCHEMISTRY;

ENANTIOMERS;

HYDRIDES;

4 (4' FLUOROPHENYL) 3 HYDROXYMETHYL N PHENYLOXYCARBONYLPIPERIDINE; ACID ANHYDRIDE; PAROXETINE; PIPERIDINE DERIVATIVE; TRIACYLGLYCEROL LIPASE; UNCLASSIFIED DRUG;

ACYLATION; ANALYTIC METHOD; ARTICLE; CANDIDA ANTARCTICA; CATALYSIS; DRUG BINDING; DRUG PURITY; DRUG SYNTHESIS; ENANTIOMER; ENANTIOSELECTIVITY; ENZYME ACTIVE SITE; ENZYME MECHANISM; ESTERIFICATION; ISOMER; NONHUMAN; OPTICAL RESOLUTION; PROCESS OPTIMIZATION; STEREOCHEMISTRY; STRUCTURE ACTIVITY RELATION;

ACETYLATION; ANHYDRIDES; CANDIDA; CATALYSIS; ESTERIFICATION; INDICATORS AND REAGENTS; LIPASE; PAROXETINE; PIPERIDINES; SOLVENTS; STEREOISOMERISM;

EID: 0037453619     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo034120b     Document Type: Article

References (14)

1. (a) Dechant, K. L.; Clissold, S. P. Drugs 1991, 41, 225.
2. (b) Mathis, C. A.; Gerdes, J. M.; Enas, J. D.; Whitney, J. N.; Taylor, S. E.; Zahang, Y.; Mckenna, D. J.; Havlik, S.; Peroutka, S. J. J. Pharm. Pharmacol. 1992, 44, 801-805.
3. Gotor, V. Org. Proc. Res. Dev. 2002, 6, 420-426.
4. (a) De Gonzalo, G.; Brieva, R.; Sánchez, V. M.; Bayod, M.; Gotor, V. J. Org. Chem. 2001, 66, 8947-8953.
5. (b) Bayod, M.; Sánchez, V. M.; de Gonzalo, G.; Brieva, R.; Gotor, V. U.S. Patent 2003/0018048 to Astur Pharma.
6. Santaniello, E.; Reza-Elahi, S.; Ferraboschi, P. Chiral Synthons by Enzymatic Acylation and Esterification Reactions. In Topics in Current Chemistry; Fessner, W.D., Ed.; Springer-Verlag: Berlin, Germany, 1999; Vol. 200, pp 415-460.
7. Bianchi, D.; Cesti, P.; Battistel, E. J. Org. Chem., 1988, 53, 5531-5534.
8. Terao, Y.; Tsuji, K.; Murata, M.; Achiwa, K.; Nishio, T.; Watanabe, N.; Seto, K. Chem. Pharm. Bull. 1989, 37, 1653.
9. Goswami, A.; Howell, J. M.; Hua, E. Y.; Mirfakhrae, K. D.; Soumeillant, C. M.; Swaminathan, S.; Qian, X.; Quiroz, F.; Vu, T. C.; Wang, X.; Zheng, B. Org. Proc. Res. Dev. 2001, 5, 415-420.
10. Bayod, M.; Sánchez, V. M.; de Gonzalo, G.; Brieva, R.; Gotor, V. ES Patent P200202916 to Astur Pharma.
11. Chen, C. S.; Fujimoto, Y.; Girdaukas, G.; Sih, C. J. J. Am. Chem. Soc. 1982, 104, 7294.
12. Kiso, Y.; Hirokawa, T. Chem. Lett. 1980, 323-326.
13. Dubey, S. N.; Baweia, R. K.; Puri, D. M. J. Indian Chem. Soc. 1982, 59, 1133-1135.
14. 13C NMR spectra are given in the Supporting Information. The degree of purity is indicated by the inclusion of elemental analysis.