Versatile Acylation of N-Nucleophiles Using a New Polymer-Supported 1-Hydroxybenzotriazole Derivative

Journal of Organic Chemistry

Volumn 62, Issue 8, 1997, Pages 2594-2603

  Pop, Iuliana E ^a   Déprez, Benoît P ^a   Tartar, André L ^b  

^a CEREP   (France)

^b CNRS   (France)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000745360     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961761g     Document Type: Article

References (33)

1. Bunin, B. A.; Ellman, J. A. J. Am. Chem. Soc. 1992, 114, 10997.
2. Hobbs DeWitt, S.; Kiely, J. S.; Stankovic, C. J.; Schroeder, M. C.; Reynolds Cody, D. M.; Pavia, M. R. Proc. Natl. Acad. Sci. U.S.A. 1993, 90, 6909.
3. Hobbs DeWitt, S.; Schroeder, M. C.; Stankovic, C. J.; Strode, J. E.; Czarnic, A. W. Drug Dev. Res. 1994, 35, 116.
4. Rano, T. A.; Chapman, K. T. Tetrahedron Lett. 1995, 36, 3789.
5. Deshpande, M. S. Tetrahedron Lett. 1994, 55, 5613.
6. Forman, F. W.; Sucholeiki, I. J. Org. Chem. 1995, 60, 523.
7. Yu, K.-L.; Deshpande, M. S.; Vyas, D. M. Tetrahedron. Lett. 1994, 35, 8919.
8. Hiroshige, M.; Hauske, J. R.; Zhou, P. Tetrahedron. Lett. 1995, 36, 4567.
9. Chen, C.; Ahlberg Randall, L. A.; Miller, R. B.; Jones, A. D.; Kurth, M. J. J. Am. Chem. Soc. 1994, 116, 2661.
10. Fridkin, M.; Patchornic, A.; Katchalski, E. J. Am. Chem. Soc. 1965, 87, 4646.
11. Fridkin, M.; Patchornic, A.; Katchalski, E. J. Am. Chem. Soc. 1966, 88, 3164.
12. Kalir, R.; Fridkin, M.; Patchornic, A. Eur. J. Biochem. 1974, 42, 151.
13. Fridkin, M.; Hazum, E.: Kalir, R.: Rotman, M.; Koch, Y. J. Solid- Phase Biochem. 1977, 2, 175.
14. Kalir, R.; Warshawsky, A.; Fridkin, M.; Patchornic, A. Eur. J. Biochem. 1975, 59, 55.
15. Mokotoff, M.; Patchornic, A Int. J. Pept. Protein Res. 1983, 21, 145.
16. Mokotoff, M.; Zhao, M.; Roth, S. M.; Slavosky, J. N; Shelley, J. A. J. Med. Chem. 1990, 33, 354.
17. Weinshenker, A.; Shen, C.-M. Tetrahedron Lett. 1972, 3281.
18. Desai, M. C.; Stephens Straminello, L. M. Tetrahedron Lett. 1993, 34, 7685.
19. Shai, Y.; Jacobson, K. A.; Patchornic, A. J. Am. Chem. Soc. 1985, 107, 4249.
20. McKenzie, W. M.; Sherrington, D. C. Journal of Polymer Science: Polymer Chemistry Edition; John Wiley & Sons, Inc., 1982; Vol. 20.
21. Harrison, C. R.; Hodge, P.; Hunt, B. J.; Khoshedel, E.; Richardson, G. J. Org. Chem. 1983, 48, 3721.
22. Caputo, R.; Cassano, E.; Longobardo, L.; Mastroiani, D.; Palumbo, G. Synthesis 1995, 141.
23. The synthesis and use of a polymer-bound carbodiimide cationic derivative, which seems to overcome these difficulties, was meanwhile reported. 18
24. Carpino, L. A. J. Am. Chem. Soc. 1993, 115, 4397.
25. Jensen, T.-H.; Olsen, C. A.; Holm, A. J. Org. Chem. 1994, 59, 1257.
26. Carpino, L. A.; Faham, A. -E.; Minor, C. A.; Albericio, F. J. them. Soc., Chem. Commun. 1994, 201.
27. Wijkmans, J. C. H. M.; Blok, F. A. A.; van der Marel, G. A.; van Boom, J. H.; Bloemhoff, W. Tetrahedron Lett. 1995, 36, 4643.
28. König, W.; Geiger, R. Chem. Ber. 1970, 103, 788.
29. Sarin, V. K.; Kent, B. H.; Tam, J. P.; Merrifield, R. B. Anal. Biochem. 1981, 117, 147.
30. Koppel, I.; Koppel, J.; Leito, I.; Pihl, V.; Grehn, L.; Ragnarsson, U. J. Chem. Res. (S) 1993, 446.
31. Frérot, E.; Coste, J.; Pantaloni, A.; Dufour, M.-N.; Jouin, P. Tetrahedron 1991, 47, 259.
32. Coste, J.; Frérot, E.; Jouin, P. Tetrahedron Lett. 1991, 32, 1967.
33. Stability studies of the polymer-bound activated ester 10a showed that, in suspension in neat DMF and in the presence of N-ethyldiisopropylamine, 62% of 10a is decomposed during 25 h to give the starting polymer 4 and the free carboxylic acid in solution. Stored under appropriate conditions, the activated esters of 4 were quite stable. After storage in dry form for two months at +4°C and under nitrogen, 10a still gave quantitative yield when reacted with phenethylamine.