Soluble polymer bound cleavage reagents: A multipolymer strategy for the cleavage of tertiary amines from REM resin

Organic Letters

Volumn 2, Issue 15, 2000, Pages 2205-2207

  Toy, Patrick H ^a   Reger, Thomas S ^a   Janda, Kim D ^a  

^a SCRIPPS RESEARCH INSTITUTE   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

AMINE; PLANT RESIN; POLYMER;

ARTICLE; CHEMISTRY; METABOLISM; SOLUBILITY;

AMINES; POLYMERS; RESINS, PLANT; SOLUBILITY;

EID: 0034720944     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol0059403     Document Type: Article

References (36)

1. (a) Brown, A. R.; Hermkens, P. H. H.; Ottenheijm, H. C. J.; Rees, D. C. Synlett 1998, 6, 817-827.
2. (b) Dolle, R. E.; Nelson, K. H., Jr. J. Comb. Chem. 1999, 1, 235-282.
3. (c) Brown, R. C. D. J. Chem. Soc., Perkin Trans. 1 1998, 3293-3320.
4. (a) Harwig, C. W.; Gravert, D. J.; Janda, K. D. Chemtracts 1999, 12, 1-26.
5. (b) Wentworth Jr., P.; Janda, K. D. Chem. Commun. 1999, 1917-1924.
6. (c) Toy, P. H.; Janda, K. D. Acc. Chem. Res. In press.
7. (a) Hori, M.; Gravert, D. J.; Wentworth Jr., P.; Janda, K. D. Bioorg. Med. Chem. Lett. 1998, 8, 2363-2368.
8. (b) Toy, P. H.; Janda, K. D. Tetrahedron Lett. 1999, 40, 6329-6332.
9. (c) Garibay, P.; Toy, P. H.; Hoeg-Jensen, T.; Janda, K. D. Synlett 1999, 7, 1438-1440.
10. (a) Booth, R. J.; Hodges, J. C. Acc. Chem. Res. 1999, 32, 18-26.
11. (b) Flynn, D. L. Med. Res. Rev. 1999, 19, 408-431.
12. (c) Parlow, J. J.; Devraj, R. V.; South, M. S. Curr. Opin. Chem. Biol. 1999, 3, 320-336.
13. (a) Frank, H.; Hagenmaier, H. Experientia 1975, 31, 131-133.
14. (b) Frank, H.; Meyer, H.; Hagenmaier, H. Chem. Ztg. 1977, 101, 188-193.
15. (c) Heusel, G.; Bovermann, G.; Gohring, W.; Jung, G. Angew, Chem., Int. Ed. Engl. 1977, 16, 642-643.
16. Han, H.; Janda, K. D. Angew. Chem., Int. Ed. Engl. 1997, 36, 6, 1731-1733.
17. (a) Morphy, J. R.; Rankovic, Z.; Rees, D. Tetrahedron Lett. 1996, 37, 3209-3212.
18. (b) Kroll, F. E. K.; Morphy, R.; Rees, D.; Gani, D. Tetrahedron Lett. 1997, 38, 8573-8576.
19. (c) Brown, A. R.; Rees, D. C.; Rankovic, Z.; Morphy, J. R. J. Am. Chem. Soc. 1997, 119, 3288-3295.
20. (d) Ouyang, X.; Armstrong, R. W.; Murphy, M. M. J. Org. Chem. 1998, 63, 1027-1032.
21. (e) Luo, Y.; Ouyang, X.; Armstrong, R. W.; Murphy, M. M. J. Org. Chem. 1998, 63, 8719-8722.
22. (f) Brown, A. J. Comb. Chem. 1999, 1, 283-285.
23. (g) Cottney, J.; Rankovic, Z.; Morphy, J. R. Biorg. Med. Chem. Lett. 1999, 9, 1323-1328.
24. (h) Yamamoto, Y.; Tanabe, K.; Okonogi, T. Chem. Lett. 1999, 103-104.
25. Kolodziej, S. A.; Hamper, B. C. Tetrahedron Lett. 1996, 37, 5277-5280.
26. Hamper, B. C.; Kolodziej, S. A.; Scates, A. M.; Smith, R. G.; Cortez, E. J. Org. Chem. 1998, 63, 708-718.
27. (a) Prien, O.; Rolfing, K.; Thiel, M.; Kunzer, H. Synlett 1997, 5, 325-326.
28. (b) Richter, H.; Walk, T.; Holtzel, A.; Jung, G. J. Org. Chem. 1999, 64, 1362-1365.
29. (c) Kulkarni, B. A.; Ganesan, A. J. Comb. Chem. 1999, 1, 373-378.
30. Kondo, Y.; Inamoto, K.; Sakamoto, T. J. Comb. Chem. 2000, 2, Articles ASAP.
31. Itsuno, S.; Sawada, T.; Hayashi, T.; Ito, K. J. Inorg. Organomet. Polym. 1994, 4, 403-414.
32. 1H NMR to be 9.5:1 (styrene: 2). This corresponds to a loading of 0.85 mmol N/g of 1. It was found that higher loaded versions of 1 were slightly soluble in methanol and the use of these polymers for amine cleavage afforded impure products.
33. JandaJel is a registered trademark of the Aldrich Chemical Co.
34. Reger, T. S.; Janda, K. D. J. Am. Chem. Soc. In press.
35. 2, methanol, hexane) and dried under vacuum. This procedure was repeated to ensure complete derivatization of the hydroxyl functional groups.
36. 2, hexane). The filtrate was concentrated to afford a white foam which was dried in vacuo. The foam was triturated with cold methanol, and the resulting slurry was filtered. The filtrate was concentrated to dry ness, and a small amount (∼5-10 mL) of cold methanol was added. The solution was filtered through a pipet containing a glass wool plug, concentrated, and dried to afford tertiary amines C in high purity.