Cl.Cl.[NH2:3][CH2:4][C@@H:5]([C:7]1[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=1)[OH:6].[Br:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][CH2:21][C:22](O)=[O:23])=[CH:16][CH:15]=1.Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1.[OH-].[Na+]>CN(C)C=O.O.C(N(CC)CC)C>[Br:13][C:14]1[CH:15]=[CH:16][C:17]([CH2:20][CH2:21][C:22]([NH:3][CH2:4][C@H:5]([OH:6])[C:7]2[CH:8]=[N:9][CH:10]=[CH:11][CH:12]=2)=[O:23])=[CH:18][CH:19]=1To 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.
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