Isavuconazole → 1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide

Participants

Reaction Steps

A mixture of 22.7 mg of 4-{2-[(1R,2R)-2-(2,5-Difluoro-phenyl)-2-hydroxy-1-methyl -3-[1,2,4]triazol-1-yl-propyl]-thiazol-4-yl}-benzonitrile and 25.0 mg of 4-tert-butoxycarbonyl-methyl-aminoacetoxy-3,5-dimethyl-benzyl bromide in CH3CN(1.5 mL) was refluxed over 15 hrs. The solvent was evaporated in vacuo and the residue was chromatographed on silica gel (Wakogel C-200, solvent:CH2Cl2/MeOH=10/1) to give 4-{4-[(tert-Butoxycarbonyl-methyl-amino)-acetoxy]-3,5 -dimethyl-benzyl)}-1-[(2R,3R)-3-[4-(4-cyano-phenyl)-thiazol-2-yl]-2-(2,5-difluoro-phenyl)-2-hydroxy-butyl]-1H-[1,2,4]triazol-4-ium bromide (36.0 mg, 84% as colorless heavy syrup);

Provenance & Evidence