The 9-Fluorenylmethoxycarbonyl Amino-Protecting Group

Journal of Organic Chemistry

Volumn 37, Issue 22, 1972, Pages 3404-3409

  Carpino, Louis A ^a   Han, Grace Y ^a  

^a UNIVERSITY OF MASSACHUSETTS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33947091567     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo00795a005     Document Type: Article

References (35)

1. For reviews see (a) E. Schröder and K. Lübke, “The Peptides,” Vol. 1, Academic Press, New York, N. Y., 1965, pp 3-51;
2. Y. Wolman in “The Chemistry of the Amino Group,” S. Patai, Ed., Interscience, New York, N. Y., 1968, Chapter 11.
3. D. A. Kidd and F. E. King, Nature (London), 162, 776 (1948);
4. J. Chem. Soc., 3315 (1949);
5. J. C. Sheehan and V. S. Franck, J. Amer. Chem. Soc., 71, 1856 (1949);
6. S. Wolfe and S. K. Hasan, Can. J. Chem., 48, 3572 (1970).
7. F. Weygand and E. Csendes, Angew. Chem., 64, 136 (1952).
8. For an alkyl-type protective group which is cleaved by methanolic ammonia, see M. Rasmussen and N. J. Leonard, J. Amer. Chem. Soc., 89, 5439 (1967).
9. A. T. Kader and C. J. M. Stirling, J. Chem. Soc., 258 (1964). We have now found that the β-tosylethyloxycarbonyl group is also cleaved under the conditions described in the present paper (liquid ammonia, ethanolamine, etc.). In the case of liquid ammonia cleavage the by-product β-tosylethyl-amine5 is easily separated from the desired amine by virtue of the insolubility of the former in ether.
10. J. Madinaveita, A. R. Martin, F. L. Rose, and G. Swain, Biochem. J., 39, 85 (1945).
11. P. J. Crowley, M. S. Thesis, University of Massachusetts, Amherst, 1958.
12. F. D. Chattaway and P. Witherington, J. Chem. Soc., 1178 (1935).
13. F. D. Chattaway, J. Chem. Soc., 355 (1936).
14. T. Wieland, G. J. Schmitt, and P. Pfaender, Justus Liebigs Ann. Chem., 694, 38 (1966).
15. A. Ceccon, U. Miotti, U. Tonellato, and M. Padovan, J. Chem. Soc. B, 1084 (1969);
16. U. Miotti, A. Sinico, and A. Ceccon, Chem. Commun., 724 (1968).
17. Cf. (a) R. A. More O'Ferrall and S. Slae, J. Chem. Soc. B, 260 (1970);
18. R. A. More O'Ferrall, J. Chem. Soc. B, 268, 274 (1970).
19. See also T. A. Spencer, M. C. R. Kendall, and I. D. Reingold, J. Amer. Chem. Soc., 94, 1250 (1972).
20. L. A. Carpino and G. Y. Han, J. Amer. Chem. Soc., 92, 5748 (1970).
21. W. G. Brown and B. A. Bluestein, J. Amer. Chem. Soc., 66, 1082 (1943).
22. Compare S. L. Johnson and D. L. Morrison, J. Amer. Chem. Soc., 94, 1323 (1972).
23. A. Sieglitz and H. Jassoy, Ber., 55, 2032 (1922).
24. For related BOC derivatives see (a) L. A. Carpino, P. H. Terry, and P. J. Crowley, J. Org. Chem., 26, 4336 (1961);
25. L. A. Carpino, B. A. Carpino, P. J. Crowley, C. A. Giza, and P. H. Terry, Org. Syn., 44, 15 (1964);
26. L. A. Carpino, D. Collins, S. Göwecke, J. Mayo, S. D. Thatte, and F. Tibbetts, Org. Syn. y 44, 20 (1964),
27. B. O. Handford, J. H. Jones, G. T. Young, and T. F. N. Johnson, J. Chem. Soc., 6814 (1965).
28. H.-D. Jakubke and A. Voight, Ber., 99, 2419 (1966).
29. Compare, D. S. Kemp, S. W. Wang, G. Busby, III, and G. Hugel, J. Amer. Chem. Soc., 92, 1043 (1970).
30. H. Wieland, F. Reindel, and J. Ferrer, Ber., 55, 3313 (1922).
31. C. H. Li, B. Gorup, D. Chung, and J. Ramachandran, J. Org. Chem., 28, 178 (1963).
32. J. G. Burr, Jr., J. Amer. Chem. Soc., 74, 1717 (1952).
33. B. A. Kent and S. Smiles, J. Chem. Soc., 422 (1934).
34. A. V. Sunthankar, B. D. Tilak, and K. Venkataraman, Proc. Indian Acad. Sci., 38A, 23 (1953);
35. Chem. Abstr., 49, 8176h (1955).