Table of Contents
ISRN Organic Chemistry
Volume 2012 (2012), Article ID 404235, 8 pages
http://dx.doi.org/10.5402/2012/404235
Research Article

N-tert-Butoxycarbonylation of Structurally Diverse Amines and Sulfamides under Water-Mediated Catalyst-Free Conditions

LCOA, Bioorganic Chemistry Group, Chemistry Department, Sciences Faculty, Badji Mokhtar-Annaba University, P.O. Box. 12, 23000 Annaba, Algeria

Received 24 January 2012; Accepted 22 February 2012

Academic Editors: B. Das, G. Li, and P. Sanchez-Andrada

Copyright © 2012 Zinelaabine Cheraiet et al. This is an open access article distributed under the Creative Commons Attribution License, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

Linked References

  1. T. W Greene and P. G. Wuts, Protective Group in Organic Synthesis, John Willey, New York, NY, USA, 4rd edition, 2007.
  2. P. J. Kocienski, Protecting Groups, George Thieme, Stuttgart, Germany, 3rd edition, 2004.
  3. C. Agami and F. Couty, “The reactivity of the n-boc protecting group: an underrated feature,” Tetrahedron, vol. 58, no. 14, pp. 2701–2724, 2002. View at Publisher · View at Google Scholar · View at Scopus
  4. B. Li, R. Bemish, R. A. Buzon et al., “Aqueous phosphoric acid as a mild reagent for deprotection of the t-butoxycarbonyl group,” Tetrahedron Letters, vol. 44, no. 44, pp. 8113–8115, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. D. S. Bose, K. K. Kumar, and A. V.N. Reddy, “A new protocol for selective deprotection of N-tert-butoxycarbonyl protective group (t-Boc) with Sn(OTf)2,” Synthetic Communications, vol. 33, no. 3, pp. 445–450, 2003. View at Publisher · View at Google Scholar
  6. N. S. Shaikh, A. S. Gajare, V. H. Deshpande, and A. V. Bedekar, “A mild procedure for the clay catalyzed selective removal of the tert- butoxycarbonyl protecting group from aromatic amines,” Tetrahedron Letters, vol. 41, no. 3, pp. 385–387, 2000. View at Publisher · View at Google Scholar · View at Scopus
  7. T. Apelqvist and D. Wensbo, “Selective removal of the n-boc protective group using silica gel at low pressure,” Tetrahedron Letters, vol. 37, no. 9, pp. 1471–1472, 1996. View at Publisher · View at Google Scholar · View at Scopus
  8. V. H. Rawal, R. J. Jones, and M. P. Cava, “Photocyclization strategy for the synthesis of antitumor agent CC-1065: synthesis of dideoxy PDE-I and PDE-II. Synthesis of thiophene and furan analogues of dideoxy PDE-I and PDE-II,” Journal of Organic Chemistry, vol. 52, no. 1, pp. 19–28, 1987. View at Google Scholar
  9. K. Nadia, B. Malika, K. Nawel, B. MedYazid, R. Zine, and N.-E. Aouf, “Simple and efficient cleavage reaction of the Boc Group in heterocyclic compounds,” Journal of Heterocyclic Chemistry, vol. 41, no. 1, pp. 57–60, 2004. View at Google Scholar
  10. Y. Basel and A. Hassner, “Di-tert-butyl dicarbonate and 4-(dimethylamino)pyridine revisited. their reactions with amines and alcohols,” Journal of Organic Chemistry, vol. 65, no. 20, pp. 6368–6380, 2000. View at Publisher · View at Google Scholar · View at Scopus
  11. E. Guibé-Jampel and M. Wakselman, “A water-soluble agent for the t-butoxycarbonylation of amines,” Journal of the Chemical Society D, no. 6, p. 267, 1971. View at Publisher · View at Google Scholar · View at Scopus
  12. G. Le Corre, E. Guibé-Jampel, and M. Wakselman, “Groupements protecteurs benzyloxycarbonyles substitues alcalinolabiles,” Tetrahedron, vol. 34, no. 20, pp. 3105–3112, 1978. View at Google Scholar
  13. S. Kim and J. Lee, “T-butyl 2-pyridyl carbonate: a useful reagent for T-butoxycarbonylation of amino acids,” Chemistry Letters, vol. 13, no. 2, pp. 237–238, 1984. View at Google Scholar
  14. G. Sennyey, G. Barcelo, and J. P. Senet, “Synthesis and use of dibenzylpyrocarbonate: preparation of dipeptide free n-benzyloxycarbonyl glycine,” Tetrahedron Letters, vol. 27, no. 44, pp. 5375–5376, 1986. View at Google Scholar · View at Scopus
  15. M. Itoh, D. Hagiwara, and T. Kamiya, “A new tert-butyloxycarbonylating reagent, 2-tert-butyloxycarbonyloxyimino-2-phenylacetoni trile,” Tetrahedron Letters, vol. 16, no. 49, pp. 4393–4394, 1975. View at Google Scholar · View at Scopus
  16. H. J. Knölker and T. Braxmeier, “Isocyanates—part 3. synthesis of carbamates by dmap-catalyzed reaction of amines with di-tert-butyldicarbonate and alcohols,” Tetrahedron Letters, vol. 37, no. 33, pp. 5861–5864, 1996. View at Publisher · View at Google Scholar · View at Scopus
  17. S. Darnbrough, M. Mervic, S. M. Condon, and C. J. Burns, “An improved synthesis of N-Boc protected aryl amines,” Synthetic Communications, vol. 31, no. 21, pp. 3273–3280, 2001. View at Publisher · View at Google Scholar
  18. D. V. Sweet, Registry of Toxic Effects of Chemical Substances 1985-86, U.S. Government Printing Office, Washington, DC, USA, 1988.
  19. A. Heydari, R. K. Shiroodi, H. Hamadi, M. Esfandyari, and M. Pourayoubi, “N-tert-butoxycarbonylation of amines using H3PW12O40 as an efficient heterogeneous and recyclable catalyst,” Tetrahedron Letters, vol. 48, no. 33, pp. 5865–5868, 2007. View at Publisher · View at Google Scholar · View at Scopus
  20. K. Shiva Kumar, J. Iqbal, and M. Pal, “Amberlyst-15: a mild, efficient and reusable heterogeneous catalyst for N-tert-butoxycarbonylation of amines,” Tetrahedron Letters, vol. 44, no. 8113–8115, pp. 385–387, 2003. View at Google Scholar
  21. F. Jahani, M. Tajbakhsh, H. Golchoubian, and S. Khaksar, “Guanidine hydrochloride as an organocatalyst for N-Boc protection of amino groups,” Tetrahedron Letters, vol. 52, no. 12, pp. 1260–1264, 2011. View at Publisher · View at Google Scholar · View at Scopus
  22. G. Bartoli, M. Bosco, A. Carlone, M. Locatelli, P. Melchiorre, and L. Sambri, “Asymmetric catalytic synthesis of enantiopure N-protected 1,2-amino alcohols,” Organic Letters, vol. 6, no. 22, pp. 3973–3975, 2004. View at Publisher · View at Google Scholar
  23. G. V. M. Sharma, J. Janardhan Reddy, P. Sree Lakshmi, and P. Radha Krishna, “Rapid and facile lewis acid catalysed boc protection of amines,” Tetrahedron Letters, vol. 45, no. 37, pp. 6963–6965, 2004. View at Publisher · View at Google Scholar · View at Scopus
  24. A. Heydari and S. E. Hosseini, “Lithium perchlorate-catalyzed boc protection of amines and amine derivatives,” Advanced Synthesis and Catalysis, vol. 347, no. 15, pp. 1929–1932, 2005. View at Publisher · View at Google Scholar · View at Scopus
  25. S. V. Chankeshwara and A. K. Chakraborti, “Copper(ii) tetrafluoroborate as a novel and highly efficient catalyst for N-tert-butoxycarbonylation of amines under solvent-free conditions at room temperature,” Tetrahedron Letters, vol. 47, no. 7, pp. 1087–1091, 2006. View at Publisher · View at Google Scholar · View at Scopus
  26. B. Das, K. Venkateswarlu, M. Krishnaiah, and H. Holla, “A highly chemoselective boc protection of amines using sulfonic-acid-functionalized silica as an efficient heterogeneous recyclable catalyst,” Tetrahedron Letters, vol. 47, no. 43, pp. 7551–7556, 2006. View at Publisher · View at Google Scholar · View at Scopus
  27. A. K. Chakraborti and S. V. Chankeshwara, “HClO4–SiO2 as a new, highly efficient, inexpensive and reusable catalyst for N-tert-butoxycarbonylation of amines,” Organic and Biomolecular Chemistry, vol. 4, no. 14, pp. 2769–2771, 2006. View at Publisher · View at Google Scholar · View at Scopus
  28. J. Akbari, A. Heydari, L. Ma'mani, and S. Hassan Hosseini, “Protic ionic liquid [TMG][Ac] as an efficient, homogeneous and recyclable catalyst for BOC protection of amines,” Comptes Rendus Chimie, vol. 13, no. 5, pp. 544–547, 2010. View at Publisher · View at Google Scholar · View at Scopus
  29. S. V. Chankeshwara and A. K. Chakraborti, “Catalyst-free chemoselective N-tert-butyloxycarbonylation of amines in water,” Organic Letters, vol. 8, no. 15, pp. 3259–3262, 2006. View at Publisher · View at Google Scholar · View at Scopus
  30. P. A. Grieco, Organic Synthesis in Water, Blackie Academic and Professional, London, UK, 1998.
  31. C.J. Li and T. H. Chang, Organic Reactions in Aqueous Medis, Wiley, New York, NY, USA, 1997.
  32. A. R. Katritzky, S. M. Allin, and M. Siskin, “Aquathermolysis: reactions of organic compounds with superheated water,” Accounts of Chemical Research, vol. 29, no. 8, pp. 399–406, 1996. View at Google Scholar · View at Scopus
  33. J. Fraga-Dubreuil and M. Poliakoff, “Organic reactions in high-temperature and supercritical water,” Pure and Applied Chemistry, vol. 78, no. 11, pp. 1971–1982, 2006. View at Publisher · View at Google Scholar
  34. N. Aouf, G. Dewynter, and J. L. Montero, “Synthesis and cyclization of carboxylsulfamides of aminoacid derivatives,” Tetrahedron Letters, vol. 32, no. 45, pp. 6545–6546, 1991. View at Publisher · View at Google Scholar · View at Scopus
  35. Z. Regaïnia, M. Abdaoui, N. E. Aouf, G. Dewynter, and J. L. Montero, “Synthesis of 1,2,5-thiadiazolidines 1,1-dioxides (cyclosulfamides) starting from amino acids and chlorosulfonyl isocyanate,” Tetrahedron, vol. 56, no. 3, pp. 381–387, 2000. View at Google Scholar · View at Scopus
  36. M. Berredjem, H. Djebbar, Z. Regainia et al., “Regiospecific synthesis and N-acylation of chiral 1,2,5-thiadiazolidines 1,1-dioxides,” Phosphorus, Sulfur and Silicon and the Related Elements, vol. 178, no. 4, pp. 693–705, 2003. View at Publisher · View at Google Scholar · View at Scopus