A One-Pot and Efficient Synthesis of Zoledronic Acid Starting from Tert-butyl Imidazol-1-yl Acetate

A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the tert -butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford in situ the corresponding...

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Bibliographic Details
Published in:Pharmaceutical chemistry journal 2015-03, Vol.48 (12), p.835-839
Main Authors: Ratrout, Samer S., Al Sarabi, Ala’eddine M., Sweidan, Kamal A.
Format: Article
Language:English
Subjects:
Acetates
Bone disorder agents
Medicine
Organic Chemistry
Pharmacology/Toxicology
Pharmacy
Phosphates
Phosphoric acid
Telomerase
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Summary:A one-pot synthesis of zoledronic acid in high yield is described. The procedure involves a non-aqueous ester cleavage of the tert -butyl imidazol-1-yl acetate under dry conditions in the presence of methanesulfonic acid as solubilizer and chlorobenzene as solvent to afford in situ the corresponding imidazolium methanesulfonate salt which yields zoledronic acid upon reaction with phosphoric acid and phosphorus oxychloride. A possible chemical mechanism for the synthesis of this acid is described.
ISSN:0091-150X
1573-9031
DOI:10.1007/s11094-015-1205-0