[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH:24]([CH3:26])[CH3:25])=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([N+:18]([O-])=[O:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9].[NH4+].[Cl-]>C(O)C.[Zn]>[CH3:1][C:2]1[NH:3][C:4]([CH3:27])=[C:5]([C:21]([O:23][CH:24]([CH3:25])[CH3:26])=[O:22])[CH:6]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][OH:19])[CH:13]=2)[C:7]=1[C:8]([O:10][CH3:11])=[O:9]To a solution of 81 (0.75 g, 2 mmol) and NH4Cl (0.26 g, 4.85 mmol) in 86% aqueous ethanol (22 mL) was added zinc powder (0.52 g, 7.95 mmol). The resulting mixture was stirred vigorously at room temperature for 50 minutes. The mixture was filtered, and the solvent was washed with water (40 mL) and dried (MgSO4), and the solvent was removed with a rotary evaporator to obtain 0.71 g of 82 as a yellow oil which was condensed with aldehydes without further purification.
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