Cl.[NH2:2][OH:3].C(N(CC)C(C)C)(C)C.[F:13][C:14]1[CH:34]=[CH:33][C:17]([O:18][CH2:19][C:20]2[C:21]([CH2:31][OH:32])=[C:22]([OH:30])[C:23]([C:26](OC)=[O:27])=[N:24][CH:25]=2)=[CH:16][CH:15]=1>CO.CCOC(C)=O>[OH:3][NH:2][C:26]([C:23]1[C:22]([OH:30])=[C:21]([CH2:31][OH:32])[C:20]([CH2:19][O:18][C:17]2[CH:33]=[CH:34][C:14]([F:13])=[CH:15][CH:16]=2)=[CH:25][N:24]=1)=[O:27]Hydroxylamine hydrochloride (0.045 g, 0.65 mmol) and N,N-diisopropylethylamine (0.14 mL, 0.81 mmol) were added to a solution of methyl 5-((4-fluorophenoxy)methyl)-3-hydroxy-4-(hydroxymethyl)picolinate 28b (0.050 g, 0.16 mmol) in MeOH (3 mL) and heated to 70° C. for 5 h. The crude mixture was diluted with EtOAc and washed with saturated aqueous ammonium chloride solution and brine. The organic extract was dried (Na2SO4), filtered and concentrated in vacuo to afford the title compound (0.048 g, 96%): LC-MS (M+H)+ m/z 309.
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