Acetic Acid → HCID 178500506, compound

Reaction equation

[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7]([NH2:9])[CH3:8].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH:17]([C:22](=O)[CH3:23])[C:18]([O:20][CH3:21])=[O:19].C(O)(=O)C>CO>[O:1]1[CH2:6][CH2:5][O:4][CH2:3][CH:2]1[CH:7](/[N:9]=[C:22](\[CH3:23])/[CH:17]([C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[Br:10])[C:18]([O:20][CH3:21])=[O:19])[CH3:8]

Participants

Procedure

To a solution of 1-(1,4-dioxan-2-yl)ethanamine (2.5 g, 19 mmol) in methanol (100 mL) was added methyl 2-(2-bromophenyl)-3-oxobutanoate (5.4 g, 20 mmol) and acetic acid (1.8 g, 30 mmol). The resulting reaction system was warm to reflux and allowed to stir overnight. The reaction mixture was concentrated and purified by column chromatographed on silica gel (eluted: dichloromethane/methanol 50:1→20:1→5:1) the title compound (1 g, 14%) as a brown solid. LCMS (M+H+) m/z: calcd. 383.07. found 384.9.