Peptide coupling in the presence of highly hindered tertiary amines

Journal of Organic Chemistry

Volumn 61, Issue 7, 1996, Pages 2460-2465

  Carpino, Louis A ^a   Ionescu, Dumitru ^a,b   El Faham, Ayman ^a,c  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

^b UNIVERSITY OF BUCHAREST   (Romania)

^c Alexandria University Faculty Of Science   (Egypt)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001012518     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo950912x     Document Type: Article

References (50)

1. Carpino, L. A. J Am. Chem. Soc. 1993, 115, 4397.
2. For a list of some of these new reagents as well as current structural assignments and nomenclature, see: (a) Carpino, L. A.; El-Faham, A.; Minor, C. A.; Alberecio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203. (b) Abdelmoty, I.; Albericio, F.; Carpino, L. A,; Foxman, B. M.; Kates, S. A. Lett. Peptide Sci. 1994, 1, 57-67. Whether HAPyU crystallizes in the form shown (2) or in the isomeric guanidinium form (comparable to structure 1 for HATU) is not yet known. In the absence of appropriate X-ray data structure 2 is arbitrarily retained in the present paper.
3. For a list of some of these new reagents as well as current structural assignments and nomenclature, see: (a) Carpino, L. A.; El-Faham, A.; Minor, C. A.; Alberecio, F. J. Chem. Soc., Chem. Commun. 1994, 201-203. (b) Abdelmoty, I.; Albericio, F.; Carpino, L. A,; Foxman, B. M.; Kates, S. A. Lett. Peptide Sci. 1994, 1, 57-67. Whether HAPyU crystallizes in the form shown (2) or in the isomeric guanidinium form (comparable to structure 1 for HATU) is not yet known. In the absence of appropriate X-ray data structure 2 is arbitrarily retained in the present paper.
4. a data, unless otherwise indicated, are taken from: Perrin, D. Dissociation Constants of Organic Bases in Aqueous Solution; Butterworths: London, 1965: Supplement, 1972.
5. Carpino, L. A.; El-Faham, A. J. Org. Chem. 1994, 59, 695.
6. (a) Gold, V. In Progress in Stereochemistry; de la Mare, P. B. D., Klyne, W., Eds.; Butterworths: Washington, 1962; Vol. 3, p 169.
7. (b) Feather, J. A.; Gold, V. Proc. Chem. Soc. 1963, 306; J. Chem. Soc. 1965, 1752.
8. (b) Feather, J. A.; Gold, V. Proc. Chem. Soc. 1963, 306; J. Chem. Soc. 1965, 1752.
9. (c) Covitz, F.; Westheimer, F. H. J. Am. Chem. Soc. 1963, 85, 1773.
10. (d) Hine, J.; Houston, J. G.; Jensen, J. H.; Mulders, J. J. Am. Chem Soc. 1965, 87, 5050.
11. (e) Lewis, E. S.; Funderburk, L, H. J. Am. Chem. Soc. 1967, 89, 2322.
12. (f) Gutsche, C. D.; Redmore, D.; Buriks, R. S.; Nowotny, K.; Grassner, H.; Armbruster, L. W. J. Am. Chem. Soc. 1967, 89, 1235.
13. (g) Zollinger, H. Helv. Chim. Acta 1955, 38, 1623.
14. Carpino, L. A.; El-Faham, A.; Albericio, F. J. Org. Chem. 1995, 60, 3561.
15. Wenschuh, H.; Beyermann, M.; Haber, H.; Seydel, J. K.; Krause, E.; Bienert, M.; Carpino, L. A.; El-Faham, A. J. Org. Chem. 1995, 60, 405.
16. Balaban, A. T ; Nenitzescu, C. D. Liebigs Ann. Chem. 1959, 625, 74.
17. Brown, H. C.; Kanner, B. J. Am. Chem. Soc. 1966, 88, 986.
18. Ikekawa, N.; Sato, Y.; Maeda, T. Chem. Pharm. Bull. 1954, 2, 205.
19. Thummel, R. P.; Kohli, D. K. J. Org. Chem. 1977, 42, 2742.
20. Tsuda, K.; Ikekawa, N.; Mishima, H.; Iino, A. Chem. Pharm. Bull. 1953, 1, 122.
21. 16 Thus, it may not be unexpected that differences among α-substituted pyridines in the reactions examined here will be muted except for the most bulky substituents.
22. Shug, J. C.; Viers, J. W.; Seeman, J. I. J. Org. Chem. 1983, 48, 4892.
23. Seeman, J. I.; Schug, J. C.; Viers, J. W. J. Org. Chem. 1983, 48, 2399.
24. Weber, H.; Pant, J.; Liedigk, M.; Wunderlich, H. Chem. Ber. 1981, 114, 1455.
25. Seeman, J. I.; Galzerno, R.; Curtis, K.; Schug, J. C.; Viers, J. W. J. Am. Chem. Soc. 1981, 103, 5982.
26. Balaban, A. T.; Bota, A.; Chiraleur, F.; Sliam, E.; Hanes, A.; Draghici, C. Rev. Roum. Chim. 1977, 22, 1003.
27. An example of such an effect has been reported for proton sponge. See: Alder, R. W.; Goode, N. C.; Miller, N.; Hibbert, F.; Hunte, K. P. P.; Robbins, H. J. J. Chem. Soc., Chem. Commun. 1978, 89.
28. Although increases in solvent polarity are often associated with increased loss of configuration in peptide coupling the true nature of the effect is more complex. For a review see: Benoiton, N. L. In The Peptides; Gross, E., Meienhofer, J., Eds.; Academic: New York, 1983; Vol. 5, Part B, p 276.
29. Burfield, D. R.; Smithers, R. H. J. Org. Chem. 1978, 43, 3966.
30. -2 1) (Ritchie, C. D. In Physical Organic Chemistry, 2nd ed.; Dekker: New York, 1990; p 209). Relationships of this type may be responsible for the poor activation of carboxylic acids sometimes observed in DMF which may show effects similar to those seen in DMSO.
31. -2 1) (Ritchie, C. D. In Physical Organic Chemistry, 2nd ed.; Dekker: New York, 1990; p 209). Relationships of this type may be responsible for the poor activation of carboxylic acids sometimes observed in DMF which may show effects similar to those seen in DMSO.
32. -2 1) (Ritchie, C. D. In Physical Organic Chemistry, 2nd ed.; Dekker: New York, 1990; p 209). Relationships of this type may be responsible for the poor activation of carboxylic acids sometimes observed in DMF which may show effects similar to those seen in DMSO.
33. -2 1) (Ritchie, C. D. In Physical Organic Chemistry, 2nd ed.; Dekker: New York, 1990; p 209). Relationships of this type may be responsible for the poor activation of carboxylic acids sometimes observed in DMF which may show effects similar to those seen in DMSO.
34. Hopkins, H. P., Jr., Jahagirdar, D. V.; Moulik, P. S ; Aue, D. H.; Webb, H. M.; Davidson, W. R.; Pedley, M. D. J. Am. Chem. Soc. 1984, 106, 4341.
35. Arnett, E. M.; Chawla, B. J. Am. Chem. Soc. 1979, 101, 7141.
36. Potts, K. T.; Winslow, P. A. Synthesis 1987, 839.
37. Deutsch, E.; Cheung, N. K. V. J. Org. Chem. 1973, 38, 1123.
38. Bernasconi, C. F ; Carré, D. J. J. Am. Chem. Soc. 1979, 101, 2707.
39. a values of related amines see: Essery, J. M.; Schofield, K. J. Chem. Soc. 1961, 3939.
40. a values of related amines see: Essery, J. M.; Schofield, K. J. Chem. Soc. 1961, 3939.
41. Barton, D. H. R.; Elliott, J. D.; Gero, S. D. J. Chem. Soc., Perkin Trans. 1 1982, 2085.
42. (a) Kuffner, F.; Koechlin, W. Monatsh. Chem. 1962, 93, 476.
43. (b) Bock, H.; Goebel, I.; Havlas, Z.; Liedle, S.; Oberhammer, H. Angew. Chem., Int. Ed. Engl. 1991, 30, 187.
44. (c) Wong, T. C.; Collazo, L. R.; Guziec, F. S., Jr. Tetrahedron 1995, 51, 649.
45. Cook, M. J.; Katritzky, A. R. Maños, M. M. J. Chem. Soc 1971, 1330.
46. Carpino, L. A.; El-Faham, A. J. Am. Chem. Soc. 1995, 117, 5401-5402.
47. King, L. C.; Ozog, F. J. J. Org. Chem. 1955, 20, 448.
48. King, L. C.; Ozog, F. J.; Moffat, J. J. Am. Chem. Soc. 1951, 73, 300.
49. The conditions described for the synthesis of the 4-piperidinopyrrylium salt and its reaction with ammonia/ammonium carbonate were adopted. See: Anker, R. M.; Cook, A. H. J. Chem. Soc. 1946, 117.
50. For the precursor (1,4-dihydro-3,5-dicarbethoxy-2,6-dimethylpyridine), see: Singer, A.; McElvain, S. M. In Organic Syntheses; Blatt, A. H., Ed.; Wiley: New York; 1943; Collect. Vol. 2, p 214.