Hydrochloric Acid → HCID 66868248, compound

Participants

Reaction Steps

To a solution of methyl 4-[(1S)-1-({[1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinolin-8-yl]carbonyl}amino)ethyl]benzoate (129 mg) in THF (2.0 mL) and methanol (1.0 mL) was added a 1 M aqueous sodium hydroxide solution (1.0 mL) at room temperature, followed by stirring for 2 days. The reaction mixture was neutralized by adding 1 M hydrochloric acid (1.0 mL) at room temperature, followed by extraction with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate). The resulting product was dissolved in ethyl acetate (2.0 mL), and to the solution was added a 4 M hydrogen chloride ethyl acetate solution (2.0 mL) at room temperature, followed by stirring for 1 day. The solvent was evaporated under reduced pressure, and the residue was washed with ethyl acetate, collected by filtration, and dried under reduced pressure to obtain 4-[(1S)-1-({[1-(4-chlorobenzyl)-1,2,3,4-tetrahydroquinolin-8-yl]carbonyl}amino)ethyl]benzoic acid hydrochloride (97 mg).

Provenance & Evidence