Benzyl mercaptan → HCID 89444621, compound

Participants

Reaction Conditions

Reaction Steps

Benzylmercaptan (1.5 eq.) and 1-[3,5-bis(trifluoromethyl)phenyl]-3-[(1R,2R)-2-(dimethylamino)cyclohexyl]thiourea (0.01 eq.) were added to a solution of tert-butyl 4-[(E)-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-but-2-enoyl]-2-methyl-benzoate (200 mg) in toluene (1.5 mL) at −40° C. The solution was stirred at −40° C. for 6 hours then at room temperature for 17 hours. The reaction was quenched by the addition of a saturated solution of sodium chloride, and then extracted with ethylacetate. The collected organic phases were dried over magnesium sulfate, filtered and the filtrate was evaporated under vacuo. The residue was purified by chromatography on silica gel (eluent: cyclohexane/ethyl acetate) to give tert-butyl 4-[3-benzylsulfanyl-3-(3,5-dichlorophenyl)-4,4,4-trifluoro-butanoyl]-2-methyl-benzoate (205 mg) as a mixture of two enantiomers.

Provenance & Evidence