tert-Butanol → tert-butyl 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorophenylcarbamate

Participants

Reaction Conditions

Reaction Steps

To a suspension of 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorobenzoic acid (540 mg) in a mixture of toluene (5 mL) and t-BuOH (1.5 mL) cooled to 0° C. was added diphenyl phosphoryl azide (DPPA) (302 mg, 1.1 eq) followed by DIPEA (1.3 eq, 0.23 mL). During addition of base, white slurry became clear solution. Reaction mixture was heated at 80° C. overnight. LC-MS showed complete conversion. After cooling to ambient temperature, the reaction mixture was diluted with EtOAc and washed with satd NaHCO3. The organic layer was dried, concentrated and purified by chromatography (silica, EtOAc/Hex, 10-60%) to yield tert-butyl 3-chloro-4-((5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-ylthio)methyl)-5-fluorophenylcarbamate (230 mg). MS (EI) m/z 634 (MH+).

Provenance & Evidence