Phenacyl bromide → 3-{4-[(4-{[Benzyl(4-phenyl-1,3-thiazol-2-yl)amino]-methyl}benzyl)oxy]phenyl}propanoic acid

Participants

Reaction Conditions

Reaction Steps

A mixture of 2-bromo-1-phenylethanone (100 mg), N-benzylthiourea (83 mg) and N,N-dimethylformamide (2 mL) was stirred at 80° C. for 1 hr. The reaction mixture was cooled to 0° C., sodium hydride (60% in oil, 80 mg) was added, and the mixture was stirred at room temperature for 30 min. Methyl 3-(4-{[4-(chloromethyl)benzyl]oxy}phenyl)propanoate (300 mg) was added to the reaction mixture at room temperature, and the mixture was stirred at room temperature for 1 hr. The reaction mixture was poured into water and extracted with ethyl acetate. The ethyl acetate layer was dried using a Presep Dehydration tube (manufactured by Wako Pure Chemical Industries, Ltd.) and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:19-1:0 in volume ratio) to give the title compound (110 mg, yield 41%) as colorless crystals.

Provenance & Evidence