Sodium Hydroxide → HCID 69103320, compound

Participants

Reaction Steps

To a mixture of (1R)-2-amino-1-(3-pyridyl)ethanol dihydrochloride (260 g), (4-bromophenyl)acetic acid (278 g), 1-hydroxybenzotriazole (175 g) and 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride (248 g) in N,N-dimethylformamide (1.3 l) was added triethylamine (361 l) at ambient temperature for 1 hour. The mixture was stirred at room temperature overnight. To the mixture was added water (1.3 l). The mixture was poured into water (1.6 l) and basified with 24% aqueous sodium hydroxide solution. The mixture was stirred at room temperature for 5 hours. The precipitate was collected by filtration, washed with water and dried in vacuo to give 2-(4-bromophenyl)-N-[(2R)-2-hydroxy-2-(3-pyridyl)ethyl]acetamide (335 g).

Provenance & Evidence