Triethylamine → HCID 67953258, compound

Participants

Reaction Steps

To a solution of (2S,4S)-1-(3-chloro-5-trifluoromethyl-pyridin-2-yl)-4-hydroxy-pyrrolidine-2-carboxylic acid (5-tert-butyl-isoxazol-3-yl)-amide (183 mg, 0.423 mmol) in dimethyl sulfoxide (5 mL) is added triethylamine (0.118 mL, 0.846 mmol) and sulfur trioxide pyridine complex (115 mg, 0.72 mmol). The reaction is stirred at room temperature for 4 hours. More triethylamine (0.18 mL, 1.27 mmol) and sulfur trioxide pyridine complex (155 mg, 0.97 mmol) are added to the reaction mixture and the stirring is continued for another 2 hours. The reaction is quenched with 1N hydrochloric acid aqueous solution and the solid precipitated out of the solution is filtered and dissolved in dichloromethane and washed with saturated sodium bicarbonate aqueous solution and brine, dried over Na2SO4, filtered and concentrated under reduced pressure. Purification by chromatography on silica eluting with ethyl acetate/hexanes and further purification using pre LC-MS provides the title compound, ESI m/z 431 [M+H+].

Provenance & Evidence