Hydrochloric Acid → HCID 3720342, compound

Participants

Reaction Steps

2-Amino-3-(4-fluorophenyl)propionic acid methyl ester (2.01 g), p-toluenesulfonyl chloride (2.25 g), and 4-dimethylaminopyridine (309 mg) were dissolved in chloroform (30 mL), and pyridine (3.0 mL) was added thereto, followed by heating under reflux for 4.5 hours. Additional p-toluenesulfonyl chloride (2.20 g) was added thereto, and the thus-obtained mixture was heated under reflux for 3.5 hours. The reaction mixture was poured into ice and 1N HCl (17 mL) to partition the mixture. The organic layer was sequentially washed with saturated aqueous sodium hydrogencarbonate and saturated brine, and was dried over sodium sulfate anhydrate. The solvent was distilled away under reduced pressure, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=9:1->2:1), to thereby give the title compound (2.89 g).

Provenance & Evidence