Trifluoroacetic acid → HCID 67080070, compound

Participants

Reaction Steps

Trifluoroacetic acid (8.03 g, 70.4 mmol) was added at 0° C. to a solution of {(S)-1-[((S)-3-benzyloxy-1-methoxymethyl-propyl)-(2,2-dimethoxy-ethyl)-carbamoyl]-ethyl}-carbamic acid tert-butyl ester (2.20 g, 4.69 mmol) in dichloromethane (40 mL). The reaction mixture was allowed to reach room temperature over 2 h, then triethylsilane (2.73 g, 70.4 mmol) was added. The reaction mixture was stirred for 16 h at room temperature, then cooled to 0° C. and treated with triethylamine (7.24 g, 70.4 mmol). After 10 min the ice bath was removed and the reaction mixture evaporated. The residue was taken up in ethyl acetate/water and neutralized with 2 M aq. sodium carbonate solution. The organic layer was washed with brine, dried (MgSO4), filtered, and evaporated. Chomatography (SiO2; dichloromethane-methanol gradient) afforded the title compound (735 mg, 51%). Light yellow oil, MS (ISP)=307.3 (M+H)+.

Provenance & Evidence