Trifluoroacetic acid → HCID 86673301, compound

Participants

Reaction Steps

To a stirred solution of (2R)-methyl 2-((2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)amino)-3-(tritylthio)propanoate (24.8 g; 44.8 mmol) in anhydrous dichloromethane (200 mL), previously cooled to in an ice-water bath under nitrogen, was added trifluoroacetic acid (14 mL; 20.7 g; 182 mmol; 405 mole %), followed by triethylsilane (14.4 mL; 10.5 g; 90.1 mmol; 200 mole %). The reaction mixture was stirred at ambient temperature for 2 h then concentrated in vacuo. The residue was redistilled from dichloromethane and the residue absorbed onto silica gel (30 g). The absorbed sample was applied to a column of SiO2 (660 g) and eluted with 2% ethyl acetate in hexane, gradually increased to 10% EtOAc in hexane to give 11.74 g (84.5%) of (2R)-methyl 3-mercapto-2-((2,2,2-trifluoro-1-(4-fluorophenyl)ethyl)amino)propanoate which was used directly in the next step. LC-MS, negative ion mode: m/z=310 [M−H]− (100%).

Provenance & Evidence