Ammonia → HCID 58026166, compound

Participants

Reaction Steps

To a solution of 14.2 g of 2-((S)-1,1-dimethyl-3-triethylsilanyloxy-3-trifluoromethylhex-5-ynyl)-5-fluorobenzoic acid (0.030 mol) in 400 mL of DCM was added 4.6 mL of pyridine (0.057 mol) followed by 3.3 mL of thionyl chloride (0.045 mol). The reaction was stirred for 25 minutes then carried on to next step. The crude acid chloride was cannulated into a flask containing ammonia (7 M in MeOH, 185 mL, 1.30 mol). The mixture was stirred for 40 minutes then quenched with saturated aqueous sodium bicarbonate solution. The mixture was then diluted with 20 mL of ethyl acetate, washed with two 100 mL portions of saturated aqueous sodium bicarbonate solution, dried over magnesium sulfate, filtered, and concentrated in vacuo. The crude mixture was chromatographed on silica gel using 0-50% ethyl acetate/hexanes to afford 7.1 g (50%) of 2-((S)-1,1-dimethyl-3-triethylsilanyloxy-3-trifluoromethylhex-5-ynyl)-5-fluorobenzamide.

Provenance & Evidence