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

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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 .
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