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An Economical and Facile Method to Synthesize Vildagliptin
Corresponding Author(s) : Xiangnan Hu
Asian Journal of Chemistry,
Vol. 26 No. 18 (2014): Vol 26 Issue 18
Abstract
A facile and economical synthetic method to prepare vildagliptin with three steps was reported. It was started from L-proline via successful reaction with chloroacetyl chloride in tetrahydrofuran to afford 1-(2-chloroacetyl)-pyrrolidine-2-carboxylic acid, followed by reacting with 2-chloro-4,6-dimethoxy-1,3,5-triazine, N-methyl morpholine and 2,4,6-trichloro-1,3,5-triazine to give 1-(2-chloroacetyl)-pyrrolidine-2-carbonitrile which was reacted with 3-aminoadmantanol to get the target compound of vildagliptin.
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- E. Sebokova, A. Christ, M. Boehringer and J. Mizrahi, Curr. Top. Med. Chem., 7, 547 (2007); doi:10.2174/156802607780091019.
- D.J. Drucker, S.I. Sherman, F.S. Gorelick, R.M. Bergenstal, R.S. Sherwin and J.B. Buse, Diabetes Care, 33, 428 (2010); doi:10.2337/dc09-1499.
- C.F. Deacon, Diabetes, 53, 2181 (2004); doi:10.2337/diabetes.53.9.2181.
- C.W. Chia and J.M. Egan, Drug Discov. Today Dis. Mech., 2, 295 (2005); doi:10.1016/j.ddmec.2005.08.013.
- E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell and T.E. Hughes, J. Med. Chem., 46, 2774 (2003); doi:10.1021/jm030091l.
- S.K. Singh, N. Manne and M. Pal, Beilstein J. Org. Chem., 4, (2008); doi:10.3762/bjoc.4.20.
- S. Manne, E. Sajja, V.R. Ghojala and K.R. Bairy, Process for Preparation of DPP- IV Inhibitors, WO Patent 2011/101861 A1 (2011).
- J. Peng, Y. Feng, Z. Tao, Y. Chen and X. Hu, Lett. Org. Chem., 10, 159 (2013); doi:10.2174/1570178611310030003.
- H.L. Rayle and L. Fellmeth, Org. Process Res. Dev., 3, 172 (1999); doi:10.1021/op980097y.
- G. Blotny, Tetrahedron, 62, 9507 (2006); doi:10.1016/j.tet.2006.07.039.
- A. El-Faham and F. Albericio, Chem. Rev., 111, 6557 (2011); doi:10.1021/cr100048w.
- J.R. Dudley, J.T. Thurston, F.C. Schaefer, D. Holm-Hansen, C.J. Hull and P. Adams, J. Am. Chem. Soc., 73, 2986 (1951); doi:10.1021/ja01151a003.
- W. Stephen, Process for Preparing Vildagliptin, WO Patent 0,084,383 (2008).
References
E. Sebokova, A. Christ, M. Boehringer and J. Mizrahi, Curr. Top. Med. Chem., 7, 547 (2007); doi:10.2174/156802607780091019.
D.J. Drucker, S.I. Sherman, F.S. Gorelick, R.M. Bergenstal, R.S. Sherwin and J.B. Buse, Diabetes Care, 33, 428 (2010); doi:10.2337/dc09-1499.
C.F. Deacon, Diabetes, 53, 2181 (2004); doi:10.2337/diabetes.53.9.2181.
C.W. Chia and J.M. Egan, Drug Discov. Today Dis. Mech., 2, 295 (2005); doi:10.1016/j.ddmec.2005.08.013.
E.B. Villhauer, J.A. Brinkman, G.B. Naderi, B.F. Burkey, B.E. Dunning, K. Prasad, B.L. Mangold, M.E. Russell and T.E. Hughes, J. Med. Chem., 46, 2774 (2003); doi:10.1021/jm030091l.
S.K. Singh, N. Manne and M. Pal, Beilstein J. Org. Chem., 4, (2008); doi:10.3762/bjoc.4.20.
S. Manne, E. Sajja, V.R. Ghojala and K.R. Bairy, Process for Preparation of DPP- IV Inhibitors, WO Patent 2011/101861 A1 (2011).
J. Peng, Y. Feng, Z. Tao, Y. Chen and X. Hu, Lett. Org. Chem., 10, 159 (2013); doi:10.2174/1570178611310030003.
H.L. Rayle and L. Fellmeth, Org. Process Res. Dev., 3, 172 (1999); doi:10.1021/op980097y.
G. Blotny, Tetrahedron, 62, 9507 (2006); doi:10.1016/j.tet.2006.07.039.
A. El-Faham and F. Albericio, Chem. Rev., 111, 6557 (2011); doi:10.1021/cr100048w.
J.R. Dudley, J.T. Thurston, F.C. Schaefer, D. Holm-Hansen, C.J. Hull and P. Adams, J. Am. Chem. Soc., 73, 2986 (1951); doi:10.1021/ja01151a003.
W. Stephen, Process for Preparing Vildagliptin, WO Patent 0,084,383 (2008).