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Synthetic Communications
An International Journal for Rapid Communication of Synthetic Organic Chemistry
Volume 41, 2011 - Issue 18
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Original Articles

Amberlyst-15 Catalyzed Cbz Protection of Amines Under Solvent-Free Conditions

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Pages 2674-2683 | Received 26 Apr 2010, Published online: 29 Jun 2011

REFERENCES

  • Fieser, L. F., Maligres, P. E., Houpis, I., Rossen, K., Molinga, A., Sager, J., Upadhyay, V., Wells, K. M., Reamer, R. A., and Lynch, J. E.Askin, D., Volante, R. P., Reiderr, P. I., Berkowit, D. B., Pedersen, M. L., Bergmann, M., Zervas, L., , 1967. "Carbobenzoxy chloride". In: Reagents for Organic Synthesis. Vol. 1. New York: John Wiley and Sons; 1967. pp. 109–110(a), (b), Synthesis of the optically active spiroindoline-based growth hormone secretagogue. Tetrahedron 1997, 32, 10983–10992, (c), Simultaneous amino and carboxyl group protection for α-branched amino acids. J. Org. Chem. 1994, 59, 5476–5478, (d), A general process for synthesis of peptides. Ber. Dtsch. Chem. Ges. 1932, 65, 1192–1201.
  • Moura, S., Pinto, E., Fuchs, S., Kapp, T., Otto, H., Schoeneberg, T., Francke, P., Gust, R., Schlueter, A. D., Barney, C. L., Huber, E. W., McCarthy, J. R., Recuero, V., Gonzalo, G., Brieva, R., Gotor, V., Bergeron, R. J., Ludin, C., Muller, R., Smith, R. E., Phanstiel, O., Adinolfi, M., Barone, G., Guariniello, L., Iadonosi, A., Teshima, T., Nakajima, K., Takahashi, M., Shiba, T., Myers, A. G., Gin, D. Y., Rogers, D. H., Watkins, B. E., Rapoport, H., Saito, H., Yamada, T., Okumura, K., Yonezawa, Y., Shin, C.-G., Durand, P., Richard, P., Renaut, P., Won, C.-Y., Chu, C.-C., Lee, J. D., , 2007. One-pot synthesis of N-Cbz-I_BMAA and derivatives from N-Cbz-I-serine, Tetrahedron Lett. 48 (2007), pp. 2325–2327, (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k), (l).
  • Harnandez, J. N., and Martin, V. S., 2004. First practical protection of α-amino acids as N,N-benzyloxy carbonyl drerivatives, J. Org. Chem. 69 (2004), pp. 3590–3592.
  • Pavan Kumar, V., Somi Reddy, M., Narender, K., and Rama Rao, K., 2006. Aqueous phase monoprotection of amines and amino acids as N-benzyloxycarbonyl derivatives, Tetrahedron Lett. 47 (2006), pp. 6393–6396.
  • Gawande, M. B., Polshettiwar, V., Varma, R. S., and Jayaram, R. V., 2007. An efficient and chemoselective Cbz protection of amines using silica–sulfuric acid at room temperature, Tetrahedron Lett. 48 (2007), pp. 8170–8173.
  • Chinni Mahesh, M., Narasimhulu, M., Srikanth Reddy, T., Suryakiran, N., and Venkateswarlu, Y., 2007. A mild and efficient chemoselective protection of amines as N-benzyloxycarbonyl derivatives in the presence of La(NO3)3 · 6H2O under solvent-free conditions, Tetrahedron Lett. 48 (2007), pp. 55–59.
  • Varala, R., Enugala, R., and Adapa, S. R. I., 2007. Molecular iodine–catalyzed efficient N-Cbz protection of amines, Iranian Chem. Soc. 4 (2007), pp. 370–374.
  • Shrikhande, J. J., Gawande, M. B., and Jayram, R. V., 2008. A catalyst-free N-benzyloxycarbonylation of amines in aqueous media at room temperature, Tetrahedron Lett. 49 (2008), pp. 4799–4803.
  • Vanladinpuia, K., and Bez, G., 2010. An excellent method for Cbz protection of amines, Chem. Lett. (2010), pp. 228–229.
  • Petchmanee, T., Ploypradith, P., Ruchirawat, S., Zipp, G. G., Hilfiker, M. A., Nelson, S. G., Ploypradith, P., Cheryklin, P., Niyomtham, N., Bertoni, D. R., Ruchirawat, S., Yadav, G. D., and Pathre, G. S.Young, J.-J., Jung, L.-J., Cheng, K.-M., Farhanullah, , Sharon, A., Maulik, P. R., Ram, V. J., Schinzer, D., Kabbara, J., Ringe, K., Shiva Kumar, K., Iqbal, J., Pal, M., Yadav, J. S., Subba Reddy, B. V., Vishnumurthy, P., Coppola, G. M., Tajbakhsh, M., Heydari, A., Khalilzadeh, M. A., Lakouraj, M., Zamenian, B., Khaksar, S., , 2006. Solid-supported acids for debenzylation of aryl benzyl ethers, J. Org. Chem. 71 (2006), pp. 2892–2895, (a), (b), (c), (d), (e), (f), (g), (h), (i), (j), (k).
  • Kawai, A., Hara, O., Yamada, Y., and Shiari, T., 1988. Stereoselective synthesis of the hydroxyl amino acid moiety of Al-77-B, a gastroprotective substance from Bacillus pumilus Al-77, Tetrahedron Lett. 29 (1988), pp. 6331–6334.

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