Sodium Hydroxide → HCID 69103236, compound

Participants

Reaction Steps

To a suspension of (1R)-2-amino-1-(3-pyridyl)ethanol dihydrochloride (2.90 g), 3-(4-bromophenyl)propionic acid (3.30 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (2.77 g) and 1-hydroxybenzotriazole hydrate (2.92 g) in N,N-dimethylformamide (30 ml) was added triethylamine (4.02 ml) at 4° C. The mixture was stirred at room temperature for 1.5 hours. The reaction mixture was poured into water (145 ml) and the pH was adjusted to 10 with 24% aqueous sodium hydroxide solution at 4° C. The mixture was stirred at room temperature for 30 minutes. The precipitate was collected by filtration, washed with water and dried at 50° C. to give 3-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]propanamide (4.32 g) as a white solid. The filtrate was extracted with ethyl acetate, washed with water and brine and dried over magnesium sulfate. Filtration followed by evaporation under reduced pressure gave 3-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]propanamide (0.43 g) as a white solid.

Provenance & Evidence