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A Convenient Synthesis of Carbapenem Antibiotic Ertapenem Sodium
Corresponding Author(s) : Yuan-Zhen Xiong
Asian Journal of Chemistry,
Vol. 26 No. 12 (2014): Vol 26 Issue 12
Abstract
A convenient synthesis of ertapenem sodium is described. The starting material, trans-hydroxyproline, was converted to N-diisopropoxyphosphoryl hydroxyproline (5), mesylation of the hydroxyl group and activation of the carboxyl group in 5 by using methanesulfonyl chloride afforded intermediate 6, aminolysis of the mixed anhydride 6 with allyl 3-aminobenzoate gave compound 8, treatment of the methanesulfonate (8) with potassium thioacetate gave key intermediate compound 4. The compound 4 was deacetylated and then coupled with enol phosphate 2, followed by cleavage of protecting groups affording ertapenem in an overall yield of 39.2 %.
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- (a) K.M.J. Brands, R.B. Jobson, K.M. Conrad, J.M. Williams, B. Pipik, M. Cameron, A.J. Davies, P.G. Houghton, M.S. Ashwood, I.F. Cottrell, R.A. Reamer, D.J. Kennedy, U.H. Dolling and P.J. Reider, J. Org. Chem., 67, 4771 (2002); doi:10.1021/jo011170c.; (b) E. Boselli, D. Breilh, M.C. Saux, J.B. Gordien and B. Allaouchiche, Intensive Care Med., 32, 2059 (2006); doi:10.1007/s00134-006-0401-5.
- W.G. Song, Y. Xia and H. Fang, Zhongguo Yaoye, 18, 87 (2009).
- J.M. Williams, K.M.J. Brands, R.T. Skerlj, R.B. Jobson, G. Marchesini, K.M. Conrad, B. Pipik, K.A. Savary, F.R. Tsay, P.G. Houghton, D.R. Sidler, U.H. Dolling, L.M. DiMichele and T.J. Novak, J. Org. Chem., 70, 7479 (2005); doi:10.1021/jo0501442.
- K.M.J. Brands, K. Wiedbrauk, J.M. Williams, U.H. Dolling and P.J. Reider, Tetrahedron Lett., 39, 9583 (1998); doi:10.1016/S0040-4039(98)02300-4.
- M. Sunagawa, H. Matsumura and T. Bando, Heterocycles, 41, 147 (1995); doi:10.3987/COM-94-6920.
- (a) Y. F. Zhang, H. Chen, J. H. Peng, R. C. Gao, G. M. Zhang, J. Chin. Pharm. Univ., 38, 305 (2007); (b) Y. Shi, K. Li, X.B. Zhao, J. Lu and X.W. Sun, Zhongguo Kangshengsu Zazhi, 36, 519 (2011).
- K.M.J. Brands, G. Marchesini, J.M. Williams, U.H. Dolling and P.J. Reider, Tetrahedron Lett., 37, 2919 (1996); doi:10.1016/0040-4039(96)00447-9.
- J.H. Chapman and L.N. Owen, J. Chem. Soc., 579 (1950); doi:10.1039/jr9500000579.
- T. Legrand, S. Chhun, E. Rey, B. Blanchet, J.R. Zahar, F. Lanternier, G. Pons and V. Jullien, J. Chromatogr. B, 875, 551 (2008); doi:10.1016/j.jchromb.2008.09.020.
- J.P. Huang, X.X. Chen, S.X. Gu, L. Zhao, W.X. Chen and F.E. Chen, Org. Process Res. Dev., 14, 939 (2010); doi:10.1021/op100094p.
References
(a) K.M.J. Brands, R.B. Jobson, K.M. Conrad, J.M. Williams, B. Pipik, M. Cameron, A.J. Davies, P.G. Houghton, M.S. Ashwood, I.F. Cottrell, R.A. Reamer, D.J. Kennedy, U.H. Dolling and P.J. Reider, J. Org. Chem., 67, 4771 (2002); doi:10.1021/jo011170c.; (b) E. Boselli, D. Breilh, M.C. Saux, J.B. Gordien and B. Allaouchiche, Intensive Care Med., 32, 2059 (2006); doi:10.1007/s00134-006-0401-5.
W.G. Song, Y. Xia and H. Fang, Zhongguo Yaoye, 18, 87 (2009).
J.M. Williams, K.M.J. Brands, R.T. Skerlj, R.B. Jobson, G. Marchesini, K.M. Conrad, B. Pipik, K.A. Savary, F.R. Tsay, P.G. Houghton, D.R. Sidler, U.H. Dolling, L.M. DiMichele and T.J. Novak, J. Org. Chem., 70, 7479 (2005); doi:10.1021/jo0501442.
K.M.J. Brands, K. Wiedbrauk, J.M. Williams, U.H. Dolling and P.J. Reider, Tetrahedron Lett., 39, 9583 (1998); doi:10.1016/S0040-4039(98)02300-4.
M. Sunagawa, H. Matsumura and T. Bando, Heterocycles, 41, 147 (1995); doi:10.3987/COM-94-6920.
(a) Y. F. Zhang, H. Chen, J. H. Peng, R. C. Gao, G. M. Zhang, J. Chin. Pharm. Univ., 38, 305 (2007); (b) Y. Shi, K. Li, X.B. Zhao, J. Lu and X.W. Sun, Zhongguo Kangshengsu Zazhi, 36, 519 (2011).
K.M.J. Brands, G. Marchesini, J.M. Williams, U.H. Dolling and P.J. Reider, Tetrahedron Lett., 37, 2919 (1996); doi:10.1016/0040-4039(96)00447-9.
J.H. Chapman and L.N. Owen, J. Chem. Soc., 579 (1950); doi:10.1039/jr9500000579.
T. Legrand, S. Chhun, E. Rey, B. Blanchet, J.R. Zahar, F. Lanternier, G. Pons and V. Jullien, J. Chromatogr. B, 875, 551 (2008); doi:10.1016/j.jchromb.2008.09.020.
J.P. Huang, X.X. Chen, S.X. Gu, L. Zhao, W.X. Chen and F.E. Chen, Org. Process Res. Dev., 14, 939 (2010); doi:10.1021/op100094p.