Deprotection of N-tert-butoxycarbonyl (Boc) groups in the presence of tert-butyl esters

Author:

Lin Linus S,Lanza Thomas,de Laszlo Stephen E,Truong Quang,Kamenecka Theodore,Hagmann William K

Publisher

Elsevier BV

Subject

Organic Chemistry,Drug Discovery,Biochemistry

Reference10 articles.

1. Greene, T. W.; Wuts, P. G. M. Protective Groups in Organic Synthesis, 2nd Ed.; John Wiley & Sons: New York, 1991.

2. Bodanszky, M.; Bodanszky, A. The Practice of Peptide Synthesis, 2nd Ed.; Springer-Verlag: Berlin, 1994.

3. (a) Gibson, F. S.; Bergmeier, S. C.; Rapoport, H. J. Org. Chem. 1994, 59, 3216.

4. (b) For the use of HCl/dioxane in solid-phase applications, see: Hruby, V.; Tamaki, M.; Han, G. Abstracts of Papers; 219th National Meeting of the American Chemical Society, San Francisco, CA; American Chemical Society: Washington DC, 2000; ORG 140. Two other isolated cases were reported in the context of total synthesis. See: Grieco, P. A.; Hon, Y. S.; Perez-Medrano, A. J. Am. Chem. Soc. 1988, 110, 1630 (TBSOTf/lutidine; K2CO3/MeOH); Baldwin, J. E.; Adlington, R. M.; Godfrey, C. R. A.; Gollins, D. W.; Schofield, C. J. Tetrahedron 1991, 47, 5835 (TsOH/MeOH).

5. Wright, S. W.; Hageman, D. L.; Wright, A. S.; McClure, L. D. Tetrahedron Lett. 1997, 38, 7345.

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