N[C:2]1[S:3][C:4]2[CH:10]=[C:9]([O:11][CH3:12])[C:8]([Cl:13])=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].BrC[C:18]([CH2:26][CH3:27])([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20].Cl>O>[NH2:6][C:5]1[CH:7]=[C:8]([Cl:13])[C:9]([O:11][CH3:12])=[CH:10][C:4]=1[S:3][CH2:2][C:18]([CH2:26][CH3:27])([CH2:22][CH2:23][CH2:24][CH3:25])[C:19]([OH:21])=[O:20]To a suspension of 4 (20.0 g) in H2O (200 ml) was added KOH (100 g). The slurry was refluxed for 7 h and allowed to cool to RT. To the dark solution was added 2 (33.2 g) in one portion. The reaction mixture was stirred for 18 h at which point the pH was adjusted to 4 with HCl. The mixture was transferred to a separatory funnel and extracted three times with ethyl acetate. The organic layer was dried and concentrated. The product was purified by column chromatography on silica gel eluting the product with 10% ethyl acetate/petroleum ether giving 5 (30.1 g).
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