Hydrochloric Acid → 2,3-Dihydroxybutanedioic Acid

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Co-crystals of itraconazole HCl and tartaric acid were prepared. Approximately 212.7 mg of L-tartaric acid and 118 microL of 37% HCl were dissolved in 25 mL of hot dioxane. This solution was added to 1.0 g of cis-itraconazole dissolved in 50 mL of hot dioxane with stirring. The mixture was heated until a clear solution formed and was then allowed to cool to room temperature. Upon cooling, 50 mL tert-butyl methyl ether was added and the crystals were harvested by vacuum filtration on a Buchner funnel with #4 Whatman filter paper. The crystals were washed 3 times with 5 mL aliquots of cold tert-butyl methyl ether and left to air dry. Approximately 573 mg of a crystalline form of cis-itraconazole HCl-tartaric acid (1:1:0.5) co-crystal were obtained. (See FIGS. 20 and 21)

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