Journal
GREEN PROCESSING AND SYNTHESIS
Volume 3, Issue 2, Pages 111-116Publisher
WALTER DE GRUYTER GMBH
DOI: 10.1515/gps-2013-0107
Keywords
carboxylic acids; dronic acid derivatives; optimization; phosphorus trichloride; synthesis
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Funding
- Gedeon Richter Plc.
- Hungarian Scientific and Research Fund (OTKA) [K83118]
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According to literature, the synthesis of dronic acid derivatives from the corresponding carboxylic acids using phosphorus trichloride and phosphorous acid as the P-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.
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