N-bromobutanimide → HCID 22494074, compound

Reaction equation

[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:23][CH:24]([CH3:26])[CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)[CH3:2].[Br:28]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:23][CH:24]([CH3:26])[CH3:25])[CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:10]([OH:13])=[C:11]([Br:28])[CH:12]=1)[CH3:2]

Participants

Procedure

402 mg of 3-(3-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester was dissolved in 5 ml of acetonitrile, and 200 mg of N-bromosuccinimide was added thereto, followed by stirring for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 433 mg of 3-(3-bromo-5-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester from fractions eluted with hexane-ethyl acetate (5:1).