[CH3:1][O:2][C:3]1[N:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[NH2:12][C:13]1[CH:14]=[C:15]([CH:21]=[CH:22][CH:23]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17].O.O=[CH:26][C:27]([OH:29])=[O:28]>C(#N)C>[CH2:19]([O:18][C:16]([C:15]1[CH:14]=[C:13]([NH:12][CH:26]([C:6]2[CH:7]=[N:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:27]([OH:29])=[O:28])[CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:20]A mixture of 6-methoxypyridin-3-ylboronic acid (1.2 g, 7.84 mmol), ethyl 3-aminobenzoate (1.29 g, 7.84 mmol), and 2-oxoacetic acid hydrate (723 mg, 7.84 mmol) in acetonitrile (70 ml) was stirred at room temperature overnight. The solvent was evaporated under vacuum, and the crude product was purified by flash chromatography (DCM/MeOH=9/1) to obtain 2-(3-(ethoxycarbonyl)phenylamino)-2-(6-methoxypyridin-3-yl)acetic acid (0.95 g, 38% yield).
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