Convenient protection of amines as carbamates using polymer-bound HOBT as catalyst

(Note: The full text of this document is currently only available in the PDF Version )

Kleanthis G. Dendrinos and Aristotle G. Kalivretenos


Abstract

A method for the facile protection of primary and secondary amines as carbamate (Cbz, Fmoc and t-Boc) derivatives using polymer bound 1-hydroxybenzotriazole (HOBT) is reported.


References

  1. For recent reviews, see: (a) N. K. Terrett, M. Gardner, D. W. Gordon, R. J. Kobylecki and J. Steele, Tetrahedron, 1995, 51, 8135 CrossRef CAS; (b) ‘Special Issue: Combinatorial Chemistry’Acc. Chem. Res., 1996, 29, 111 Search PubMed; (c) ‘Combinatorial Chemistry: synthesis and application’ ed. S. R. Wilson and A. W. Czarnik, Wiley, New York, 1997; (d) ‘Combinatorial peptide and nonpeptide libraries: a handbook’ ed. G. Jung, VCH, New York, 1996.
  2. (a) K.-L. Yu and M. S. Deshpande, Tetrahedron Lett., 1994, 35, 8919 CrossRef CAS; (b) T. A. Rano and K. T. Chapman, Tetrahedron Lett., 1995, 36, 3789 CrossRef CAS; (c) F. W. Forman and I. Sucholeiki, J. Org. Chem., 1995, 60, 523 CrossRef CAS; (d) B. J. Backes, A. A. Virgilio and J. A. Ellman, J. Am. Chem. Soc., 1996, 118, 3055 CrossRef CAS; (e) M. A. Marx, A. Grillot, C. T. Louer, K. A. Beaver and P. A. Bartlett, J. Am. Chem. Soc., 1997, 119, 6153 CrossRef CAS; (f) E. J. Kantorowski and M. J. Kurth, J. Am. Chem. Soc., 1997, 119, 6797; (g) B. Hinzen and S. V. Ley, J. Chem. Soc., Perkin Trans. 1, 1998, 1 RSC.
  3. R. Kalir, A. Warshawsky, M. Fridkin and A. Patchornik, Eur. J. Biochem., 1975, 59, 55 CAS.
  4. (a) I. E. Pop, B. P. Déprev and A. L. Tartar, J. Org. Chem., 1997, 62, 2594–2603 CrossRef CAS; (b) K. G. Dendrinos and A. G. Kalivretenos, Chem. Commun., 1998, 499 RSC.
  5. D. A. Laufer, T. M. Chapman, D. I. Marlborough, V. M. Vaidya and E. R. Blout, J. Am. Chem. Soc., 1968, 90, 2696–2698 CrossRef CAS.
  6. (a) A. Weinshenker and C.-M. Shen, Tetrahedron Lett., 1972, 3281 CrossRef CAS; (b) M. C. Desai and L. M. Stephens Stramiello, Tetrahedron Lett., 1993, 34, 7685 CrossRef CAS.
  7. (a) L. D. Arnold, H. I. Assil and J. C. Vederas, J. Am. Chem. Soc., 1989, 111, 3973 CrossRef CAS; (b) R. Caputo, E. Cassano, L. Longobardo, D. Mastroiani and G. Palumbo, Synthesis, 1995, 141 CrossRef CAS.
  8. W. Huang and A. G. Kalivretenos, Tetrahedron Lett., 1995, 36, 9113 CrossRef CAS.
  9. K. G. Dendrinos and A. G. Kalivretenos, Tetrahedron Lett., 1998, 39, 1321 CrossRef CAS.
Click here to see how this site uses Cookies. View our privacy policy here.