Hydrochloric Acid → HCID 70654524, compound

Participants

Reaction Steps

A solution of {(RS)-5-[5-(benzhydrylidene-amino)-2-fluoro-phenyl]-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-yl}-[bis-(4-methoxy-phenyl)-phenyl-methyl]-amine (207 mg, 263 μmol) in dichloromethane (10 ml) was treated with trifluoroacetic acid (1.01 ml, 13.1 mmol). The orange colored solution was stirred at room temperature for 1 hour. In order to cleave the intermediate benzophenonimine, hydrochloric acid (1M, 2.63 ml) and dioxane (10 ml) were added. The mixture was stirred at 23° C. for 4 hours. For the workup, the reaction mixture was poured into an aqueous solution of sodium carbonate (1 M) followed by the extraction with dichloromethane. The organic layer was washed with brine, dried over sodium sulfate and evaporated. The crude product was purified by chromatography on silica gel using a 110:10:1-mixture of dichloromethane, methanol and ammonium hydroxide as the eluent. The (RS)-5-(5-amino-2-fluoro-phenyl)-5-difluoromethyl-1,1-dioxo-2,5,6,7-tetrahydro-1H-1λ6-[1,4]thiazepin-3-ylamine (72 mg, 85% yield) was obtained as a light brown foam. MS (ISP): m/z=322.0 [M+H]+.

Provenance & Evidence