Lithium Hydroxide → HCID 58897144, compound

Participants

Reaction Steps

To benzyl 1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethylcarbamothioylcarbamate (269 mg, 0.483 mmol) in Methanol/THF (2 mL/2 mL) was added LiOH (2M, 483 mL, 0.966 mmol). The reaction was refluxed for 40 minutes. The solvents were removed and the residue dissolved in EtOAc. The resulting solution was washed with H2O, brine, dried over MgSO4 and concentrated. The crude mixture was purified by silica gel ISCO chromatography (12 g column) using hexanes/EtOAc (0-50% over 18 min) to give 1-(1-(5-chloropyridin-2-yl)-1-(3-fluoro-5-(trifluoromethyl)phenyl)-2-phenylethyl)thiourea as a pale yellow foam (169 mg, 78% yield). LCMS: 3.8 min [M+1] 454.2 (4 min gradient, MeOH/H2O 0.1% TFA); 1H NMR (400 MHz, CDCl3) δ ppm 5.62 (s, 3H), 6.71 (d, J=7.34 Hz, 3H), 7.11 (d, J=8.56 Hz, 6H), 7.32 (s, 2H), 7.50-7.57 (m, 1H), 7.69 (dd, J=8.56, 2.20 Hz, 1H), 8.28 (s, 1H), 8.64 (s, 1H).

Provenance & Evidence