[Cl:1][C:2]1[C:3]([CH3:22])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[C:16](N(OC)C)=[O:17])(=[O:10])=[O:9].[H-].C([Al+]CC(C)C)C(C)C.[Cl-].[NH4+]>O1CCCC1>[Cl:1][C:2]1[C:3]([CH3:22])=[N:4][O:5][C:6]=1[NH:7][S:8]([C:11]1[CH:15]=[CH:14][S:13][C:12]=1[CH:16]=[O:17])(=[O:9])=[O:10]
To a mixture of 3-[(4-chloro-3-methyl-1,2-oxazol-5-yl)sulfamoyl]-N-methoxy-N-methylthiophene-2-carboxamide described in Production Example 1-2 (8.0 g, 22 mmol) and tetrahydrofuran (160 mL), was added dropwise diisobutyl aluminum hydride (46 mL, 48 mmol, 1.0 M n-hexane solution) at −78° C., followed by stirring at 0° C. for 30 minutes. A saturated aqueous solution of ammonium chloride was added dropwise at 0° C. to the reaction mixture, which was then gradually allowed to warm to room temperature and stirred for 1 hour at that temperature. The reaction mixture was filtered with Celite, and water was added to the filtrate, which was then extracted with ethyl acetate. The organic layer was washed with brine, and the solvent was distilled away under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:methanol=30:1) to give the title compound (5.1 g, 75% yield).
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