[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]#[N:17])[CH2:11][C:10]3([O:15][CH2:14][CH2:13][O:12]3)[CH2:9]2)=[CH:4][CH:3]=1.[OH:18]O.[NH4+].[OH-]>CO.O>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:16]([NH2:17])=[O:18])[CH2:9][C:10]3([O:12][CH2:13][CH2:14][O:15]3)[CH2:11]2)=[CH:4][CH:3]=1To a mixture of Compound [XXXIII] (13.0 g, 44.2 mmol, 1.0 eq.) in MeOH (520 mL) was added H2O2 (13.7 mL, 33% in water, 133 mmol, 3.00 eq.), and NH4OH (52 mL). The resulting mixture was stirred for 16 hours at room temperature, then diluted with additional water and extracted with ethyl acetate (×3). The combined organics were washed with Na2S2O3 (10% in water), dried, and concentrated. The residue was purified by silica gel chromatography by eluting with heptane and ethyl acetate (gradient of 0% to 100% EtOAc) to give Compound [XXXIV]: LCMS (m/e) 312, 314 (M+H); 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.78-2.87 (m, 2H) 3.22-3.29 (m, 2H) 3.84-3.91 (m, 2H) 3.91-3.99 (m, 2H) 5.42 (br. s., 2H) 7.19-7.25 (m, 2H) 7.48-7.55 (m, 2H).
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