Liquid-phase synthesis with solid-phase workup: Application to multistep and combinatorial syntheses

Journal of Organic Chemistry

Volumn 64, Issue 6, 1999, Pages 2110-2113

  Perrier, Hélène ^a   Labelle, Marc ^a  

^a MERCK FROSST CENTRE FOR THERAPEUTIC RESEARCH   (Canada)

Author keywords

[No Author keywords available]

Indexed keywords

QUINOLINE;

CHEMICAL REACTION; NOTE; PRECIPITATION; SOLID PHASE EXTRACTION; SOLUBILITY; SYNTHESIS;

EID: 0033583107     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9809074     Document Type: Note

References (12)

1. Ellman, J. A. Acc. Chem. Res. 1998, 29, 132-143 and references therein.
2. For a review of this type of optimization, see: Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. Tetrahedron 1996, 13, 4527-4554.
3. Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc., 1996, 118, 2567-2573.
4. Kim, R. M.; Manna, M.; Hutchins, S. M.; Griffin, P. R.; Yates, N. A.; Bernick, A. M.; Chapman, K. T. Proc. Natl. Acad. Sci. U.S.A. 1996, 93, 10012-10017.
5. Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419-6423. See also: Bayer, E.; Mutter, M. Nature, 1972, 237, 512-513.
6. Han, H.; Wolfe, M. M.; Brenner, S.; Janda, K D. Proc. Natl. Acad. Sci. U.S.A. 1995, 92, 6419-6423. See also: Bayer, E.; Mutter, M. Nature, 1972, 237, 512-513.
7. Studer, A.; Hadida, S.; Ferritto, R.; Kim, S.-Y.; Jeger, P.; Wipf, P.; Curran, D. P. Science 1997, 275, 823-826.
8. This work exemplifies the concept with two ester linkers between the molecule of interest and the quinoline precipitation device. Other linkers such as silicon-based traceless linkers may also be compatible with this method and are being investigated. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498-6499. Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000. Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 16, 2703-2706.
9. This work exemplifies the concept with two ester linkers between the molecule of interest and the quinoline precipitation device. Other linkers such as silicon-based traceless linkers may also be compatible with this method and are being investigated. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498-6499. Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000. Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 16, 2703-2706.
10. This work exemplifies the concept with two ester linkers between the molecule of interest and the quinoline precipitation device. Other linkers such as silicon-based traceless linkers may also be compatible with this method and are being investigated. Boehm, T. L.; Showalter, H. D. H. J. Org. Chem. 1996, 61, 6498-6499. Chenera, B.; Finkelstein, J. A.; Veber, D. F. J. Am. Chem. Soc. 1995, 117, 11999-12000. Han, Y.; Walker, S. D.; Young, R. N. Tetrahedron Lett. 1996, 16, 2703-2706.
11. Acosta, C. K.; Bahr, M. L.; Burdett, J. E.; Cessac, J. W.; Martinez, R. A.; Rao, P. N.; Kim, H. K. J. Chem. Res. Miniprint 1991, 5, 914-934.
12. Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. A.; Grunwell, J. R.; Kaldor, S. W. Tetrahedron Lett. 1997, 19, 3357-3360.