Resolution of omeprazole by inclusion complexation with a chiral host BINOL

Tetrahedron Asymmetry

Volumn 11, Issue 8, 2000, Pages 1729-1732

  Deng, Jingen ^a   Chi, Yongxiang ^a   Fu, Fangmin ^a   Cui, Xin ^a   Yu, Kaibai ^a   Zhu, Jin ^a   Jiang, Yaozhong ^a  

^a CHENGDU INSTITUTE OF ORGANIC CHEMISTRY   (China)

Author keywords

[No Author keywords available]

Indexed keywords

OMEPRAZOLE;

ARTICLE; CHIRALITY; COMPLEX FORMATION; DRUG STRUCTURE; DRUG SYNTHESIS; ENANTIOMER; HYDROGEN BOND; PRIORITY JOURNAL;

EID: 0034607767     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0957-4166(00)00114-2     Document Type: Article

References (24)

1. Lindberg, P.; Brandstrom, A.; Wallmark, B.; Mattson, H.; Rikner, L.; Hoffmann, K. J. Med. Res. Rev. 1990, 10, 1-54.
2. Richards, A.; McCague, R. Chem. Ind. 1997, 422-425.
3. (a) Kohl, B.; Senn-Bilfinger, J. DE 4035455;
4. (b) Lindberg, P.; von Unge, S. WO 94/27988;
5. (c) von Unge, S.; Langer, V.; Sjolin, L. Tetrahedron: Asymmetry 1997, 8, 1967-1970.
6. (a) Pitchen, P.; Deshmukh, M.; Dunach, E.; Kagan, H. B. J. Am. Chem. Soc. 1984, 106, 8188-8193;
7. (b) Sigrist-Nelson, K.; Krasso, A.; Muller, R. K. M.; Fischli, A. E. Eur. J. Biochem. 1987, 166, 453-459;
8. (c) Pitchen, P.; France, C. J.; McFarlane, I. M.; Newton, C. G.; Thompson, D. M. Tetrahedron Lett. 1994, 35, 485-488;
9. (d) Larsson, M.; Stenhede, U.; Sorensen, H.; von Unge, S.; Cotton, H. WO 96/02535.
10. (a) Toda, F. Top. Curr. Chem. 1987, 140, 43-50;
11. (b) Kaupp, G. Angew. Chem., Int. Ed. Engl. 1994, 3, 728-729.
12. Zhu, J.; Qing, Y.; He, Z.; Fu, F.; Zhou, Z.; Deng, J.; Jiang, Y.; Chau, T. Tetrahedron: Asymmetry 1997, 8, 2505-2508.
13. Using (R,R)-(-)-TADDOLs 2 as chiral host, in benzene, toluene, acetonitrile, ethanol, hexane, chloroform and a mixture of benzene or toluene and hexane, no inclusion phenomena was observed.
14. Also, see: (a) Toda, F.; Tanaka, K.; Nagamatsu, S. Tetrahedron Lett. 1984, 25, 4929-4932;
15. (b) Toda, F.; Tanaka, K.; Mak, T. C. W. Chem. Lett. 1984, 2085-2088;
16. (c) Toda, F.; Mori, K. Chem. Commun. 1986, 1059-1060.
17. Condition of HPLC: KR100-5 CHI-TBB as chiral column, and hexane:2-propanol:triethylamine:acetic acid (92:8:0.15:0.05) as elute.
18. 5S: C 70.34%, N 6.65%, H 5.26%, S 5.07%; found: C 70.11%, N 6.62%, H 5.29%, S 4.91%.
19. -1.
20. Also, see: Ohishi, H.; In, Y.; Ishida, T.; Inque, M. Acta Crystallogr. 1989, C45, 1921-1923.
21. int=0.024). The direct method and successive Fourier synthesis solved the skeletal structure. All hydrogen atoms were found by the difference Fourier synthesis. Full-matrix least-squares refinement of positional and thermal parameters led to the final convergence with R=0.0577 and wR2=0.1728.
22. The formation of a supramolecular layer in the homochiral inclusion complex of lansoprazole and BINOL 3 was recently observed by an X-ray analysis: Deng, J. et al., unpublished result.
23. Hanessian, S.; Saladino, R.; Margarita, R.; Simard, M. Chem. Eur. J. 1999, 5, 2169-2183.
24. 3,4.