[CH3:1][CH:2]1[CH2:7][CH2:6][C:5](=[O:8])[O:4][C:3]1=[O:9].[NH2:10][C:11]1[CH:18]=[CH:17][C:14]([C:15]#[N:16])=[C:13]([Cl:19])[CH:12]=1.ClC1C=C(NC(=O)C(C)CCC(O)=O)C=CC=1C#N>C1(C)C=CC=CC=1.[Cl-].[Na+].O>[Cl:19][C:13]1[CH:12]=[C:11]([NH:10][C:5](=[O:8])[CH2:6][CH2:7][CH:2]([CH3:1])[C:3]([OH:4])=[O:9])[CH:18]=[CH:17][C:14]=1[C:15]#[N:16]
A solution of 3-methyldihydro-2H-pyran-2,6(3H)-dione (876 mg, 6.84 mmol), 4-amino-2-chlorobenzonitrile (1044 mg, 6.84 mmol) and TEA (0.953 mL, 6.84 mmol) in toluene (10 mL) was stirred at 70° C. for 3 hr. To the reaction mixture was added brine at room temperature, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried, and the solvent was evaporated under reduced pressure. The obtained residue was purified by COOH-silica gel column chromatography (solvent gradient; 10 to 100% ethyl acetate/hexane) to give a mixture (750 mg, 2.67 mmol, 39.1%) of 5-((3-chloro-4-cyanophenyl)amino)-2-methyl-5-oxopentanoic acid and 5-((3-chloro-4-cyanophenyl)amino)-4-methyl-5-oxopentanoic acid, as a colorless powder.
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