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Letters in Organic Chemistry

Editor-in-Chief

ISSN (Print): 1570-1786
ISSN (Online): 1875-6255

Research Article

“Greener” Synthesis of Zoledronic Acid from Imidazol-1-yl-acetic Acid and P-Reagents Using Diethyl Carbonate as the Solvent Component

Author(s): Alajos Grün, Zsuzsanna Szalai and György Keglevich*

Volume 18, Issue 1, 2021

Published on: 30 July, 2020

Page: [8 - 12] Pages: 5

DOI: 10.2174/1570178617999200730203738

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Abstract

The synthesis of a third generation dronic acid, zoledronic acid by the reaction of imidazol- 1-yl-acetic acid with phosphorus trichloride/phosphorous acid in diethyl carbonate (DEC) as a “green” solvent, and in DEC – methanesulfonic acid (MSA) solvent mixtures is described. The earlier not “green” and expensive MSA and sulfolane solvents may be replaced by DEC.

Keywords: Zoledronic acid, imidazol-1-yl-acetic acid, P-reagents, diethyl carbonate, methanesulfonic acid, sulfolane.

Graphical Abstract

[1]
Breuer, E. Fischer, J; Ganellin, C.R., Ed.; Wiley-VCH: Weinheim, 2006, pp. 371-384.
[http://dx.doi.org/10.1002/3527608001.ch18]
[2]
Romanenko, V.D. Curr. Org. Chem., 2019, 23, 530-615.
[http://dx.doi.org/10.2174/1385272823666190401141844]
[3]
Hudson, H.R.; Wardle, N.J.; Bligh, S.W.; Greiner, I.; Grün, A.; Keglevich, G. Mini Rev. Med. Chem., 2012, 12(4), 313-325.
[http://dx.doi.org/10.2174/138955712799829285] [PMID: 22303942]
[4]
Aronhime, J.; Lifshitz-Liron, R. WO20050054472005.
[5]
Rao, D.V.N.S.; Dandala, R.; Narayanan, G.K.A.S.S.; Lenin, R. Synth. Commun., 2007, 37, 4359-4365.
[http://dx.doi.org/10.1080/00397910701578545]
[6]
Pandey, S.C.; Haider, H.; Saxena, S.; Singh, M.K.; Thaper, R.K.; Dubey, S.K. US2009/3125512009.
[7]
Nagy, D.I.; Grün, A.; Greiner, I.; Keglevich, G. Curr. Org. Chem., 2017, 21, 1567-1578.
[http://dx.doi.org/10.2174/1385272821666170417122441]
[8]
Nagy, D.I.; Grün, A.; Garadnay, S.; Greiner, I.; Keglevich, G. Molecules, 2016, 21(8), 1046-1065.
[http://dx.doi.org/10.3390/molecules21081046] [PMID: 27529200]
[9]
Keglevich, G.; Grün, A.; Aradi, K.; Garadnay, S.; Greiner, I. Tetrahedron Lett., 2011, 52, 2744-2746.
[http://dx.doi.org/10.1016/j.tetlet.2011.03.093]
[10]
Garadnay, S; Grün, A.; Keglevich, G.; Neu, J. WO20121077872011.
[11]
Nagy, D.I.; Grün, A.; Lévay, K.; Garadnay, S.; Greiner, I.; Keglevich, G. Synth. Commun., 2018, 48, 663-671.
[http://dx.doi.org/10.1080/00397911.2017.1410894]
[12]
Mustafa, D.A.; Kashemirov, B.A.; McKenna, C.E. Tetrahedron Lett., 2011, 52, 2285-2287.
[http://dx.doi.org/10.1016/j.tetlet.2011.02.058]
[13]
Schäffner, B.; Schäffner, F.; Verevkin, S.P.; Börner, A. Chem. Rev., 2010, 110(8), 4554-4581.
[http://dx.doi.org/10.1021/cr900393d] [PMID: 20345182]

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