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ChemicalBook CAS DataBase List Ketoconazole
65277-42-1

Ketoconazole synthesis

7synthesis methods
Ketoconazole, cis-1-acetyl-4-[4-[2-(2,4-dichlorophenyl)-2-(1H-imidazole- 1-ylmethyl)-1,3-dioxolan-4-ylmethyl]phenyl]piperazine (35.2.4), is synthesized from 2,4-dichlorophenacyl bromide, the ketalization of which using glycerol gives cis-2-(2,4- dichlorophenyl)-2-bromoethyl-4-hydroxymethyl-1,3-dioxolane (35.2.1). Acylating the hydroxyl group of this compound with benzoyl chloride, and then alkylating the resulting compound with imidazole gives the derivative (35.2.2). Next, alkaline hydrolysis removes the benzoyl group, and a reaction with methanesulfonyl chloride gives a mesylate (35.2.3). Finally, alkylating the resulting 1-acetyl-4-(4-hydroxyphenyl)piperazine gives ketoconazole (35.2.4).

170210-42-1 Synthesis
Ketoconazole Impurity 9 (Ketoconazole Hydroxymethyl Impurity)

170210-42-1
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Yield:-

Steps:

Multi-step reaction with 2 steps
1: pyridine
2: NaH / dimethylsulfoxide / 0 - 80 °C

References:

Power, Eoin C.;Ganellin, C. Robin;Benton, David C.H. [Bioorganic and Medicinal Chemistry Letters,2006,vol. 16,# 4,p. 887 - 890]

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