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Copyright (c) 2014 Zulfiqar Ali*, Syeda Rubina Gilani, Habib Hussain, Imdad Hussain
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Conversion of Alanine and Phenylalanine into Weinreb Amides by Using Different Protecting Groups
Corresponding Author(s) : Zulfiqar Ali*
Asian Journal of Chemistry,
Vol. 26 No. 20 (2014)
Abstract
Efficient conversions of amino acids into Weinreb amides were achieved by treatment of amino acids with N, O-dimethylhydroxylamine hydrochloride in basic media. The amino group (-NH2) of amino acids were protected with p-toluene sulphonyl chloride (-OTs) and diphenyl phosphinic chloride (-dpp) to get high yield of the product. The products were purified by flash chromatography and characterized by spectroscopic techniques.
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- S. Nahm and S.M. Weinreb, Tetrahedron Lett., 22, 3815 (1981).
- (a) M.P. Sibi, Org. Prep. Proced. Int., 25, 15 (1993).; (b) M. Mentzel and H.M.R.J. Hoffmann, J. Prakt. Chem., 339, 517 (1997).; (c) J. Singh, N. Satyamurthi and I.S. Aidhen, J. Prakt. Chem., 342, 340 (2000).
- J. Jurczak and A. Golebiowski, Chem. Rev., 89, 149 (1989).
- J. M. Hamby and J. C. Hodges, Heterocycles, 35, 843 (1993).
- I. Maugras, J. Poncet and P. Jouin, Tetrahedron, 46, 2807 (1990).
- M. Braun and D. Waldmüller, Synthesis, 856 (1989).
- W. Oppolzer and A.F. Cunningham, Tetrahedron Lett., 27, 5467 (1986).
- T.W. Green and P.G.M. Wuts, Protective Groups in Organic Synthesis; John Wiley & Sons: New York (1999).
- P.J. Kocienski, Protecting Groups; Georg Thieme Verlag: Stuttgart- New York (2004).
- S.B. Sdira, C.P. Felix, M.-B.A. Giudicelli, P.F. Seigle-Ferrand, M. Perrin and R.J. Lamartine, J. Org. Chem., 68, 6632 (2003).
- Z.H. Zhou, Y.L. Tang, K.Y. Li, B. Liu and C.C. Tang, Heteroatom Chem., 14, 603 (2003).
- P.G.M. Wuts, Greene’s Protective Groups in Organic Synthesis, edn 3 (1998).
- R. Ramage, D. Hopton, M.J. Parrott, G.W. Kenner and G.A. Moore, J. Chem. Soc., Perkin Trans. 1, 1357 (1984).
References
S. Nahm and S.M. Weinreb, Tetrahedron Lett., 22, 3815 (1981).
(a) M.P. Sibi, Org. Prep. Proced. Int., 25, 15 (1993).; (b) M. Mentzel and H.M.R.J. Hoffmann, J. Prakt. Chem., 339, 517 (1997).; (c) J. Singh, N. Satyamurthi and I.S. Aidhen, J. Prakt. Chem., 342, 340 (2000).
J. Jurczak and A. Golebiowski, Chem. Rev., 89, 149 (1989).
J. M. Hamby and J. C. Hodges, Heterocycles, 35, 843 (1993).
I. Maugras, J. Poncet and P. Jouin, Tetrahedron, 46, 2807 (1990).
M. Braun and D. Waldmüller, Synthesis, 856 (1989).
W. Oppolzer and A.F. Cunningham, Tetrahedron Lett., 27, 5467 (1986).
T.W. Green and P.G.M. Wuts, Protective Groups in Organic Synthesis; John Wiley & Sons: New York (1999).
P.J. Kocienski, Protecting Groups; Georg Thieme Verlag: Stuttgart- New York (2004).
S.B. Sdira, C.P. Felix, M.-B.A. Giudicelli, P.F. Seigle-Ferrand, M. Perrin and R.J. Lamartine, J. Org. Chem., 68, 6632 (2003).
Z.H. Zhou, Y.L. Tang, K.Y. Li, B. Liu and C.C. Tang, Heteroatom Chem., 14, 603 (2003).
P.G.M. Wuts, Greene’s Protective Groups in Organic Synthesis, edn 3 (1998).
R. Ramage, D. Hopton, M.J. Parrott, G.W. Kenner and G.A. Moore, J. Chem. Soc., Perkin Trans. 1, 1357 (1984).