[CH3:1][O:2][C:3]([C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([OH:17])[CH:12]=2)[CH:8]=[CH:9][CH:10]=1)=[O:4].Br[CH2:19][CH2:20][NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23].C(=O)([O-])[O-].[K+].[K+].[Br-]>CN(C)C=O>[C:25]([O:24][C:22]([NH:21][CH2:20][CH2:19][O:17][C:13]1[CH:12]=[C:11]([C:7]2[CH:8]=[CH:9][CH:10]=[C:5]([C:3]([O:2][CH3:1])=[O:4])[CH:6]=2)[CH:16]=[CH:15][CH:14]=1)=[O:23])([CH3:28])([CH3:27])[CH3:26]A mixture of 3′-hydroxy-[1,1′-biphenyl]-3-carboxylic acid methyl ester (667 mg) and 2-bromo-1-[(tert-butoxycarbonyl)amino]ethane (980 mg) in N, N-dimethylformamide (15 mL) was treated with potassium carbonate (2.0 g). The mixture was stirred at room temperature for 30 min, and heated to 50° C. in an oil bath for 14 h. Additional bromide (396 mg) was added and the mixture was heated an additional 36 h. The mixture was cooled to room temperature and partitioned between 1:1 hexane ethyl acetate and water. The organic layer was separated, washed with water, dried over sodium sulfate, filtered and concentrated to give the crude product. Purification by silica gel chromatography (eluting with 5:1 hexane/ethyl acetate) afforded the title compound as a colorless oil (826 mg).
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