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Journal of Chemistry
Volume 2016 (2016), Article ID 9734108, 6 pages
http://dx.doi.org/10.1155/2016/9734108
Research Article

Ultrasonic-Assisted Synthesis of Two t-Butoxycarbonylamino Cephalosporin Intermediates on SiO2

1College of Chemical Engineering, Nanjing Tech University, Nanjing 210009, China
2Department of Environmental Sciences, Macquarie University, Sydney, NSW 2109, Australia

Received 16 June 2016; Accepted 28 July 2016

Academic Editor: Albert Demonceau

Copyright © 2016 Feng Xue 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. H. Ohki, K. Kawabata, S. Okuda, T. Kamimura, and K. Sakane, “FK037, a new parenteral cephalosporin with a broad antibacterial spectrum: synthesis and antibacterial activity,” Journal of Antibiotics, vol. 46, no. 2, pp. 359–361, 1993. View at Publisher · View at Google Scholar · View at Scopus
  2. K. Sakane, K. Kawabata, and H. Ohki, “Process for the preparation of cephalosporin compound,” JP 92173792, 1992.
  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. M. Lee, D. Hesek, M. Suvorov, W. Lee, S. Vakulenko, and S. Mobashery, “A Mechanism-based inhibitor targeting the DD-transpeptidase activity of bacterial penicillin-binding proteins,” Journal of the American Chemical Society, vol. 125, no. 52, pp. 16322–16326, 2003. View at Publisher · View at Google Scholar · View at Scopus
  5. Z. Y. Du, “Cefoselis sulfate intermediate and preparation method,” CN 102827190A, 2012.
  6. K. C. Lin, “Improved method for synthesizing cefoselis sulfate,” CN 1993450B, 2010.
  7. X. Y. Dai, L. W. Li, P. Guo, and C. H. Sun, “Synthesis of diphenylmethyl 7β-t-butoxycarbonylamino-3-chloromethyl-3-cephem-4-carboxylate,” Chinese Journal of Pharmaceuticals, vol. 40, pp. 16–18, 2009. View at Google Scholar
  8. D. V. Sweet, Registry of Toxic Effects of Chemical Substances 1985-86, US Government Printing Office, Washington, DC, USA, 1988.
  9. 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
  10. 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
  11. 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 & Biomolecular Chemistry, vol. 4, no. 14, pp. 2769–2771, 2006. View at Publisher · View at Google Scholar
  12. S. V. Chankeshwara and A. K. Chakraborti, “Montmorillonite K 10 and montmorillonite KSF as new and reusable catalysts for conversion of amines to N-tert-butylcarbamates,” Journal of Molecular Catalysis A: Chemical, vol. 253, no. 1-2, pp. 198–202, 2006. View at Publisher · View at Google Scholar · View at Scopus
  13. F. Jahani, M. Tajbakhsh, S. Khaksar, and M. R. Azizi, “An efficient and highly chemoselective N-Boc protection of amines, amino acids, and peptides under heterogeneous conditions,” Monatshefte für Chemie, vol. 142, no. 10, pp. 1035–1043, 2011. View at Publisher · View at Google Scholar · View at Scopus
  14. R. Varala, S. Nuvula, and S. R. Adapa, “Molecular iodine-catalyzed facile procedure for N-Boc protection of amines,” Journal of Organic Chemistry, vol. 71, no. 21, pp. 8283–8286, 2006. View at Publisher · View at Google Scholar · View at Scopus
  15. A. Heydari, S. Khaksar, and M. Tajbakhsh, “1,1,1,3,3,3-Hexafluoroisopropanol: a recyclable organocatalyst for N-Boc protection of amines,” Synthesis, vol. 19, Article ID Z11408SS, pp. 3126–3130, 2008. View at Publisher · View at Google Scholar · View at Scopus
  16. G. A. Dilbeck, L. Field, A. A. Gallo, and R. J. Gargiulo, “Biologically oriented organic sulfur chemistry. 19. Synthesis and properties of 2-amino-5-mercapto-5-methylhexanoic acid, a bishomologue of penicillamine. Use of boron trifluoride etherate for catalyzing Markownikoff addition of a thiol to an olefin,” Journal of Organic Chemistry, vol. 43, no. 24, pp. 4593–4596, 1978. View at Publisher · View at Google Scholar · View at Scopus
  17. A. Amira, H. K'tir, M. Berredjem, and N.-E. Aouf, “A simple, rapid, and efficient N-Boc protection of amines under ultrasound irradiation and catalyst-free conditions,” Monatshefte für Chemie, vol. 145, no. 3, pp. 509–515, 2014. View at Publisher · View at Google Scholar · View at Scopus
  18. S. N. Dighe and H. R. Jadhav, “Microwave assisted mild, rapid, solvent-less, and catalyst-free chemoselective N-tert-butyloxycarbonylation of amines,” Tetrahedron Letters, vol. 53, no. 43, pp. 5803–5806, 2012. View at Publisher · View at Google Scholar · View at Scopus
  19. S. Majumdar, J. De, A. Chakraborty, and D. K. Maiti, “General solvent-free highly selective N-tert-butyloxycarbonylation strategy using protic ionic liquid as an efficient catalyst,” RSC Advances, vol. 4, no. 47, pp. 24544–24550, 2014. View at Publisher · View at Google Scholar · View at Scopus
  20. A. Sarkar, S. R. Roy, N. Parikh, and A. K. Chakraborti, “Nonsolvent application of ionic liquids: organo-catalysis by 1-alkyl-3-methylimidazolium cation based room-temperature ionic liquids for chemoselective N-tert-butyloxycarbonylation of amines and the influence of the C-2 hydrogen on catalytic efficiency,” The Journal of Organic Chemistry, vol. 76, no. 17, pp. 7132–7140, 2011. View at Publisher · View at Google Scholar
  21. N. T. Tran, T. Min, and A. K. Franz, “Silanediol hydrogen bonding activation of carbonyl compounds,” Chemistry—A European Journal, vol. 17, no. 36, pp. 9897–9900, 2011. View at Publisher · View at Google Scholar · View at Scopus
  22. J. D. Sunseri, W. T. Cooper, and J. G. Dorsey, “Reducing residual silanol interactions in reversed-phase liquid chromatography: thermal treatment of silica before derivatization,” Journal of Chromatography A, vol. 1011, no. 1-2, pp. 23–29, 2003. View at Publisher · View at Google Scholar · View at Scopus