3-Bromo-4-oxo-4-phenylbutanoic acid → HCID 19603693, compound
Reaction equation
[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20](=[S:22])[NH2:21])=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:3])[CH3:2].Br[CH:24]([C:29](=O)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[CH2:25][C:26]([OH:28])=[O:27]>C(OCC)(=O)C>[C:1]([C:5]1[N:6]=[C:7]([C:10]2[O:11][C:12]3[CH:18]=[CH:17][C:16]([CH2:19][C:20]4[S:22][C:24]([CH2:25][C:26]([OH:28])=[O:27])=[C:29]([C:30]5[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=5)[N:21]=4)=[CH:15][C:13]=3[CH:14]=2)[S:8][CH:9]=1)([CH3:4])([CH3:2])[CH3:3]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
A solution of 4-tert-butyl-2-[5-(thiocarbamoylmethyl)-benzofuran-2-yl]thiazole (740 mg) and 3-bromo-4-oxo-4-phenylbutanoic acid (600 mg) in ethyl acetate (8.0 ml) was heated under reflux for 13.5 hours. After being cooled, the resulting precipitates were collected by filtration and washed with ethyl acetate. The precipitates were dissolved in ethyl acetate, washed with aqueous sodium hydrogen carbonate solution and brine, dried over magnesium sulfate and concentrated under reduced pressure to give a mixture. The mixture was subjected to column chromatography on silica gel and eluted with a mixture of chloroform, methanol and ethyl acetate (20:1:1 to 20:1:2). The fractions containing object compound were combined and concentrated under reduced pressure to give 4-tert-butyl-2-{5-[(5-carboxymethyl-4-phenylthiazol-2-yl)methyl]benzofuran-2-yl}thiazole (72 mg).