[CH3:1][C:2]([CH3:22])([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=2)[CH:11]=[CH:10][N:9]=1)=[O:6])[CH3:3].[OH:23]S([O-])(=O)=O.[K+].OO.[O-]Cl=O.[Na+]>CC#N.O.CCOC(C)=O>[CH3:3][C:2]([CH3:22])([O:4][C:5]([NH:7][C:8]1[CH:13]=[C:12]([C:14]2[CH:15]=[CH:16][C:17]([C:18]([OH:23])=[O:19])=[CH:20][CH:21]=2)[CH:11]=[CH:10][N:9]=1)=[O:6])[CH3:1]17-4 (1.0 g, 3.4 mmol) is slurried in CH3CN (40 mL). 10% KHSO4 (1.3 mL) and 30% H2O2 (0.957 mL) are added and the solution is cooled in an ice bath. NaClO2 (8.5 mmol, 770 mg) is added dropwise in 50 mL water over 20 min. The reaction is stirred for 16 hrs. The reaction mixture is diluted w/EtOAc and washed with saturated NaHCO3 (2×). The aqueous layers are combined, acidifed with 10% KHSO4, and extracted w/CH2Cl2 (2×) and EtOAc (2×) to give 17-5 as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 12.6-12.8 (bs, 1H), 9.9 (s, 1H), 8.3 (d, 1H), 8.0-8.1 (m, 3H), 7.9 (d, 2H), 7.3 (d, 1H), 1.5 (s, 9H). ##STR88## Ethyl 2-(4-(4-(2-(1,1-Dimethylethoxycarbonylamino)pyrid-4-yl)carbonylamino)phenoxy)acetate (17-6)
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