“Greener” synthesis of bisphosphonic/dronic acid derivatives

According to literature, the synthesis of dronic acid derivatives from the corresponding carboxylic acids using phosphorus trichloride and phosphorous acid as the -reactants is controversial, due to the wide range of molar ratios and diverse conditions. In this minireview, we summarize our results o...

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Bibliographic Details
Published inGreen processing and synthesis Vol. 3; no. 2; pp. 111 - 116
Main Authors Kovács, Rita, Grün, Alajos, Garadnay, Sándor, Greiner, István, Keglevich, György
Format Journal Article
LanguageEnglish
Published Berlin De Gruyter 01.04.2014
Walter de Gruyter GmbH
Subjects
Acids
Alendronic acid
Bisphosphonates
Carboxylic acids
Chlorides
Derivatives
dronic acid derivatives
Etidronic acid
Ibandronic acid
Methanesulfonic acid
optimization
Phosphorous acid
Phosphorus
phosphorus trichloride
Reviews
Risedronic acid
Synthesis
Zoledronic acid
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Summary:According to literature, the synthesis of dronic acid derivatives from the corresponding carboxylic acids using phosphorus trichloride and phosphorous acid as the -reactants is controversial, due to the wide range of molar ratios and diverse conditions. In this minireview, we summarize our results on the clarification of these problems. For example, with zoledronic acid and risedronic acid, we found that, using methanesulfonic acid (MSA) as the solvent, 3.2 equivalents of phosphorus trichloride was enough. Generalizing this optimized method, etidronate, fenidronate, ibandronate and alendronate were obtained in yields of 38%–57%, which is reasonable for valuable dronates, and in most cases, with high purities. Mechanistic aspects are also discussed.
ISSN:2191-9542
2191-9550
DOI:10.1515/gps-2013-0107