[NH2:1][C:2]1[S:6][N:5]=[C:4]([CH2:7][CH3:8])[C:3]=1[Cl:9].C[O-].[Na+].[CH3:13][CH:14]([CH3:31])[CH2:15][C:16]1[S:17][C:18]2[CH:24]=[CH:23][C:22]([CH:25]([CH3:30])[C:26](OC)=[O:27])=[CH:21][C:19]=2[N:20]=1>O1CCCC1.[Cl-].[NH4+]>[Cl:9][C:3]1[C:4]([CH2:7][CH3:8])=[N:5][S:6][C:2]=1[NH:1][C:26](=[O:27])[CH:25]([C:22]1[CH:23]=[CH:24][C:18]2[S:17][C:16]([CH2:15][CH:14]([CH3:13])[CH3:31])=[N:20][C:19]=2[CH:21]=1)[CH3:30]5-Amino-4-chloro-3-ethylisothiazole (0.81 g, 0.005 mol) was added to a suspension of sodium methoxide (0.56 g, 0.010 mol) in tetrahydrofuran (5 ml) and the mixture stirred at room temperature for 25 minutes. A solution of methyl 2-[2-(2-methylpropyl)benzothiazol-5-yl]propionate (1.15 g, 0.004 mol) in tetrahydrofuran (4 ml) was added dropwise and the mixture stirred at room temperature for 1½ hours. The mixture was diluted with saturated aqueous ammonium chloride solution and extracted with dichloromethane. The organic extract was dried over anhydrous magnesium sulfate, filtered and the filtrate evaporated in vacuo. Trituration with diethyl ether gave the desired product (1.06 g).
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