Luliconazole, PR-2699, NND-502

卢立康唑Chemical Name: (-)-(R)-(E)-2-[4-(2,4-Dichlorophenyl)-1,3-dithiolan-2-ylidene]-2-(1-imidazolyl)acetonitrile
CAS No. 187164-19-8
项目整合开发状态: Phase I
项目研究机构: Nihon Nohyaku (Originator), Bayer (Licensee)
合成路线:This compound has been obtained by two similar ways: The enantiocontrolled reduction of 2,4-dichlorophenacyl bromide (I) with BH3/THF and a chiral oxazaborole catalyst gives 1(S)-(2,4-dichlorophenyl)-2-bromoethanol (II),which is treated with Ms-Cl and TEA in dichloromethane to yield the corresponding mesylate (III).Finally,this compound is cyclized with 2-(1-imidazolyl)-3,3-disulfanylacrylonitrile (VI) by means of KOH in DMSO.Alternatively,1(S)-(2,4-dichlorophenyl)ethane-1,2-diol (VII) is treated with Ms-Cl and TEA in dichloromethane to give the corresponding dimesylate (VIII),which is condensed with the acrylonitrile (VI) with KOH as before.The intermediate acrylonitrile (VI) has been obtained by condensation of 2-(1-imidazolyl)acetonitrile (IV) with CS2 (V) by means of KOH in DMSO.