[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1.CO.C(N(CC)CC)C.[F:20][C:21]([F:28])([F:27])[C:22](OCC)=[O:23]>CCOC(C)=O>[F:20][C:21]([F:28])([F:27])[C:22]([NH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[CH:4][CH:3]=1)=[O:23]A solution of p-aminobenzoic acid in MeOH (500 mg, 3.65 mmol) was treated with 1.0 eq triethylamine (3.65 mmol, 509 μl) followed by 1.1 eq trifluoroacetic acid, ethyl ester (4.015 mmol, 478 μl). The solution was stirred overnight. The solution was diluted with EtOAc, washed with 5% KHSO4, followed by brine. The solution was dried over MgSO4 and solvent was removed by evaporation. The residue was purified by recrystallization in EtOAc/Hexane to afford eggshell-colored glossy plates (265 mg (31%), C9H6F3NO3).
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