Solution-phase parallel synthesis using ion-exchange resins

Tetrahedron

Volumn 54, Issue 16, 1998, Pages 4141-4150

  Suto, Mark J ^a   Gayo Fung, Leah M ^a   Palanki, Moorthy S S ^a   Sullivan, Robert ^a  

^a CELGENE CORPORATION   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMIDE; CARBOXYLIC ACID DERIVATIVE; ION EXCHANGE RESIN; UREA DERIVATIVE;

CONFERENCE PAPER; DRUG SYNTHESIS; ION EXCHANGE; PRIORITY JOURNAL;

EID: 0032537031     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00141-0     Document Type: Conference Paper

References (23)

1. 1. An, H.; Cummins, L. L.; Griffey, R. H.; Bharadwaj, R.; Haly, B. D.; Fraser, A. L.; Wilson-Lingardo, L.; Risen, L. M.; Wyatt, J. R.; Cook, P. D. J. Am. Chem. Soc. 1997, 119, 3696 - 3708; Whitten, J. P.; Xie, Y. F.; Erickson, P. E.; Webb, T. R.; De Souza, E. B.; Grigoriadis, D. E.; McCarthy, J. R. J. Org. Chem. 1996, 39, 4354-4357.
2. 1. An, H.; Cummins, L. L.; Griffey, R. H.; Bharadwaj, R.; Haly, B. D.; Fraser, A. L.; Wilson-Lingardo, L.; Risen, L. M.; Wyatt, J. R.; Cook, P. D. J. Am. Chem. Soc. 1997, 119, 3696 - 3708; Whitten, J. P.; Xie, Y. F.; Erickson, P. E.; Webb, T. R.; De Souza, E. B.; Grigoriadis, D. E.; McCarthy, J. R. J. Org. Chem. 1996, 39, 4354-4357.
3. 2. Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882 - 4886; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodward, S. J. Am. Chem. Soc. 1997, 119, 4874 - 4881; Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tet. Lett. 1996, 37, 7193-7196.
4. 2. Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882 - 4886; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodward, S. J. Am. Chem. Soc. 1997, 119, 4874 - 4881; Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tet. Lett. 1996, 37, 7193-7196.
5. 2. Booth, R. J.; Hodges, J. C. J. Am. Chem. Soc. 1997, 119, 4882 - 4886; Flynn, D. L.; Crich, J. Z.; Devraj, R. V.; Hockerman, S. L.; Parlow, J. J.; South, M. S.; Woodward, S. J. Am. Chem. Soc. 1997, 119, 4874 - 4881; Kaldor, S. W.; Siegel, M. G.; Fritz, J. E.; Dressman, B. A.; Hahn, P. J. Tet. Lett. 1996, 37, 7193-7196.
6. 3. Cheng, S.; Comer, D. D.; Williams, J. P.; Myers, P. L.; Boger, D. L. J. Am. Chem. Soc. 1996, 118, 2567 - 2573.
7. 4. Siegel, M. G.; Hahn, P. J.; Dressman, B. A.; Fritz, J. E.; Grunwell, J. R.; Kaldor, S. W. Tet. Lett. 1997, 38, 3357 - 3360.
8. 5. a) Gayo, L. M.; Suto, M. J. Tet. Lett. 1997,38(4), 513 - 516.
9. Other groups have also explored the use of ion-exchange resins in the production of combinatorial libraries; see b) Lawrence, R. M.; Biller, S. A.; Fryszman, O. M.; Poss, M. A.; Weller, H. A. A Simple Procedure for the Automated Solution Phase Synthesis and Purification of Non-Peptide Amides. In Conference on Molecular Diversity and Combinatorial Chemistry, January 28,1996: San Diego, CA 1996; also see references 4 and 6.
10. 6. Parlow, J. J. Tet. Lett., 1996, 37, 5257 - 5260; Parlow, J. J. Tet. Lett., 1995, 36, 1395 - 1398; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. J. Chem. Soc. Perkin Trans., 1980, 11, 2516 - 2519.
11. 6. Parlow, J. J. Tet. Lett., 1996, 37, 5257 - 5260; Parlow, J. J. Tet. Lett., 1995, 36, 1395 - 1398; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. J. Chem. Soc. Perkin Trans., 1980, 11, 2516 - 2519.
12. 6. Parlow, J. J. Tet. Lett., 1996, 37, 5257 - 5260; Parlow, J. J. Tet. Lett., 1995, 36, 1395 - 1398; Cainelli, G.; Contento, M.; Manescachi, F.; Regnoli, R. J. J. Chem. Soc. Perkin Trans., 1980, 11, 2516 - 2519.
13. 7. The ion-exchange resins described herein were purchased from Aldrich Chemical Company, inc.
14. 8. Albertson, S. Org. React., 12, 157-355, 1962; Klausner, Y. S.; Bodansky, M. Synthesis, 1972, 453-466; Wang, S. S.; Kulesha, I. D.; Winter, D. P.; Makofske, R.; Kutny, R.; Meienhofer, J. Int. J. Pept. Protein Res., 1978, 11(4), 297-300; Gross, S.; Meienhofer, J. "The Peptides," 3 vols., Academic Press, New York, 1979-1981.
15. 8. Albertson, S. Org. React., 12, 157-355, 1962; Klausner, Y. S.; Bodansky, M. Synthesis, 1972, 453-466; Wang, S. S.; Kulesha, I. D.; Winter, D. P.; Makofske, R.; Kutny, R.; Meienhofer, J. Int. J. Pept. Protein Res., 1978, 11(4), 297-300; Gross, S.; Meienhofer, J. "The Peptides," 3 vols., Academic Press, New York, 1979-1981.
16. 8. Albertson, S. Org. React., 12, 157-355, 1962; Klausner, Y. S.; Bodansky, M. Synthesis, 1972, 453-466; Wang, S. S.; Kulesha, I. D.; Winter, D. P.; Makofske, R.; Kutny, R.; Meienhofer, J. Int. J. Pept. Protein Res., 1978, 11(4), 297-300; Gross, S.; Meienhofer, J. "The Peptides," 3 vols., Academic Press, New York, 1979-1981.
17. 8. Albertson, S. Org. React., 12, 157-355, 1962; Klausner, Y. S.; Bodansky, M. Synthesis, 1972, 453-466; Wang, S. S.; Kulesha, I. D.; Winter, D. P.; Makofske, R.; Kutny, R.; Meienhofer, J. Int. J. Pept. Protein Res., 1978, 11(4), 297-300; Gross, S.; Meienhofer, J. "The Peptides," 3 vols., Academic Press, New York, 1979-1981.
18. 9. Sullivan, R.S.; Bigam, G.G.; Erdman, P.E.; Palanki, M.S.S.; Anderson, D.W.; Goldman, M.E.; Ranson, L.J.; Suto, M.J. J. Med. Chem., 1998, 41 , In Press.
19. 10. Dorfner, K. Ion Exchangers: Properties and Applications, 3rd ed.; Ann Arbor Science Publishers, inc.: Ann Arbor Science Publishers, inc.: Ann Arbor, MI, 1972; Harmer, M. A.; Hoeldrich, W. F.; Am. Chem. Soc., Div. Pet. Chem., 1997, 42(4), 763-765.
20. 10. Dorfner, K. Ion Exchangers: Properties and Applications, 3rd ed.; Ann Arbor Science Publishers, inc.: Ann Arbor Science Publishers, inc.: Ann Arbor, MI, 1972; Harmer, M. A.; Hoeldrich, W. F.; Am. Chem. Soc., Div. Pet. Chem., 1997, 42(4), 763-765.
21. 11. Smith, J., Liras, J. L., Schneider, S. E., Anslyn, E. V. J. Org. Chem., 1996, 61, 8811 - 8818.
22. 12. Kaldor, S. W.; Fritz, J. E.; Tang, J.; McKinney, E. R. Bioorg. Med. Chem. Lett., 1996, 6, 3041 - 3044.
23. 13. Gayo, L. M.; Suto, M. J. Tet. Lett., 1997, 38, 211 - 214.