Hydrochloric Acid → HCID 16124996, compound

Participants

Reaction Conditions

Reaction Steps

Ammonium chloride (6.5 mg, 0.12 mmol) in anhydrous toluene 2 ml was treated with trimethyl aluminium (in 2.0 M Hexane, 0.26 ml, 0.51 mmol) under nitrogen. After 0.25 h, It was added 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzoic acid methyl ester (50.1 mg, 0.12 mmol) in toluene 4 ml. The mixture was stirred for 3 h at 80° C. After cooling, the reaction mixture was treated with diluted HCl until no foaming more. The reaction mixture was separated with ethyl acetate and sodium bicarbonate. The organic phase was washed by brine, dried (MgSO4 anh), and concentrated. The residue was purified by preparative TLC(CH2Cl2:MeOH=15:1) to give 3-[2-(4-adamantan-1-yl-phenoxy)-acetylamino]-4-hydroxy-benzamide as a white-solid (12.9 mg, 25.6%-yield).

Provenance & Evidence