[O-]CC.[Na+].C(O[C:8](=[O:19])[C:9](=[CH:15]OCC)[C:10]([O:12][CH2:13][CH3:14])=[O:11])C.[CH:20]([NH:23][NH2:24])([CH3:22])[CH3:21].Cl>C(O)C.[Cl-].[Na+].O>[CH2:13]([O:12][C:10]([C:9]1[C:8]([OH:19])=[N:24][N:23]([CH:20]([CH3:22])[CH3:21])[CH:15]=1)=[O:11])[CH3:14]
To a solution of sodium ethoxide (23 g) in ethanol (150 mL) were added ethoxymethylene malonic acid diethyl ester (32.7 g) and isopropylhydrazine (11.2 g) at room temperature, and the mixture was stirred at 80° C. for 4 hours and then at 100° C. for 2 hours. The reaction mixture was poured into 2 mol/L hydrochloric acid (300 mL), the mixture was diluted with brine and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/5) to give the title compound (10.5 g).
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