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Candida Rugosa Lipase-catalyzed Kinetic Resolution of 3-(Isobutyryloxy)methyl 4-[2-(Difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

The lipase-catalyzed kinetic resolution of 3-(isobutyryloxy)methyl 4-[2-(difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate has been performed. The most enantioselective reaction (E = 28) was transesterification with n-butanol in water-saturated toluene at 45°C.

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REFERENCES

  1. H. Y. Aboul-Enein and I. W. Wainer, The Impact of Stereochemistry on Drug Development and Use, John Wiley & Sons, 1997, 728 pp.

  2. M. C. Hillier and P. J. Reider, Drug Discovery Today, 7, 303 (2002).

    Google Scholar 

  3. M. Strong, Food Drug Law J., 54, 463 (1999).

    Google Scholar 

  4. FDA, Chirality, 4, 338 (1992).

    Google Scholar 

  5. CPMP, Note for Guidance: Investigation of Chiral Active Substances, III/3501/91 (1993).

  6. J. M. D. Daniels, E. R. Nestmann, and A. Kerr, Drug Inf. J., 31, 639 (1997).

    Google Scholar 

  7. P. Baldrick, Drug Inf. J., 35, 99 (2001).

    Google Scholar 

  8. S. Goldmann and J. Stoltefuss, Angew. Chem., Int. Ed. Engl., 30, 1559 (1991).

    Google Scholar 

  9. Y. Tokuma and H. Noguchi, J. Chromatogr. A., 694, 181 (1995).

    Google Scholar 

  10. X. K. Holdgrun and C. J. Sih, Tetrahedron Lett., 32, 3465 (1991).

    Google Scholar 

  11. K. Achiwa and T. Kato, Curr. Org. Chem., 3, 77 (1999).

    Google Scholar 

  12. A. Sobolev, M. C. R. Franssen, B. Vigante, B. Cekavicus, N. Makarova, G. Duburs, and Ae. de Groot, Tetrahedron Asymmetry, 12, 3251 (2001).

    Google Scholar 

  13. A. Sobolev, M. C. R. Franssen, B. Vigante, B. Cekavicus, R. Zhalubovskis, H. Kooijman, A. L. Spek, G. Duburs, and Ae. de Groot, J. Org. Chem., 67, 401 (2002).

    Google Scholar 

  14. A. Sobolev, M. C. R. Franssen, J. Poikans, G. Duburs, and Ae. de Groot, Tetrahedron Asymmetry, 13, 2389 (2002).

    Google Scholar 

  15. R. R. Dubure, B. A. Vigante, J. J. Ozols, G. J. Dubur, and G. I. Rozentale, Khim. Geterotsikl. Soed., 1563 (1986).

  16. V. Petrow, J. Saper, and B. Sturgeon, J. Chem. Soc., 2134 (1949).

  17. R. R. Dubure, R. O. Vitolina, J. J. Ozols, G. J. Duburs, A. A. Kimenis, and G. V. Zarins, USSR Inventor's certificate 1018396; Chem. Abstr., 105, 191950 (1986).

    Google Scholar 

  18. B. A. Vigante, J. J. Ozol, G. O. Sileniece, A. A. Kimenis, and G. J. Dubur, USSR Inventor's certificate 794006; Chem. Abstr., 95, 704 (1981).

    Google Scholar 

  19. B. A. Vigante, J. J. Ozol, R. O. Vitolina, G. O. Sileniece, A. A. Kimenis, and G. J. Dubur, Ger. Offen. 2909852; Chem. Abstr., 94, 15579 (1981).

    Google Scholar 

  20. E. A. Bisenieks, J. R. Uldrikis, G. J. Dubur, G. D. Tirzit, A. Z. Dauvarte, A. A. Zidermane, E. V. Ivanov, and T. V. Ponomareva, USSR Inventor's certificate 1050261; Chem. Abstr., 124, 333068 (1996).

    Google Scholar 

  21. M. A. Mackanova and G. J. Vanag, Dokl. Akad. Nauk SSSR, 132, 615 (1960).

    Google Scholar 

  22. A. Sobolev, M. C. R. Franssen, N. Makarova, G. Duburs, and Ae. de Groot, Tetrahedron Asymmetry, 11, 4559 (2000).

    Google Scholar 

  23. M. Chudik, V. Mastihuba, and B. Decroix, Heterocycles, 48, 1943 (1998).

    Google Scholar 

  24. C. S. Chen, Y. Fujimoto, G. Girdaukas, and C. J. Sih, J. Am. Chem. Soc., 104, 7294 (1982).

    Google Scholar 

  25. J. A. Jongejan, J. B. A. van Tol, A. Geerlof, and J. A. Duine, Recl. Trav. Chim. Pays-Bas, 110, 247 (1991).

    Google Scholar 

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Authors
  1. A. Sobolev
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  2. R. Zhalubovskis
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  3. M. C. R. Franssen
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  4. B. Vigante
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  5. B. Chekavichus
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  6. G. Duburs
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  7. Ae. de Groot
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Sobolev, A., Zhalubovskis, R., Franssen, M.C.R. et al. Candida Rugosa Lipase-catalyzed Kinetic Resolution of 3-(Isobutyryloxy)methyl 4-[2-(Difluoromethoxy)phenyl]-2-methyl-5,5-dioxo-1,4-dihydrobenzothieno[3,2-b]pyridine-3-carboxylate. Chemistry of Heterocyclic Compounds 40, 931–937 (2004). https://doi.org/10.1023/B:COHC.0000044578.17992.95

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