1,2-Dichloroethane → 2-(4-adamantan-1-yl-phenoxy)-N-(3-methanesulfonyl-phenyl)-acetamide

Participants

Reaction Steps

To a solution of (4-adamantan-1-yl-phenoxy)-acetic acid (50 mg, 0.17 mmol), 3-methanesulfonyl-phenylamine hydrochloride (54.39 mg, 0.26 mmol) and DIPEA (33.85 mg, 0.26 mmol) in DMF (2 mL) was added EDC (50.2 mg, 0.26 mmol) and HOBt (35.39 mg, 0.26 mmol) at room temperature. The reaction mixture was stirred at room temperature until completion and then poured into water (100 mL). The resulting solid was extracted with ethyl acetate, washed with brine, aqueous sodium bicarbonate and water, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The resulting crude product was purified by flash chromatography on silica gel (Ethyl acetate:hexanes=2:8 to 4:6) to afford 2-(4-adamantan-1-yl-phenoxy)-N-(3-methanesulfonyl-phenyl)-acetamide as a colorless solid (0.61 g, 80% yield).

Provenance & Evidence