[F:1][C:2]1[C:10]([O:11][CH3:12])=[C:9]([F:13])[CH:8]=[CH:7][C:3]=1[C:4]([OH:6])=O.O1CCC[CH2:15]1.CC1C=CC=[C:37]([N+:41]([O-])=O)C=1C(OC(=O)C1C([N+]([O-])=O)=CC=CC=1C)=O.CN([C:47](=[CH2:53])[C:48]([O:50][CH2:51][CH3:52])=[O:49])C>O.C(N(CC)CC)C>[CH3:15][N:41]([CH3:37])[CH:53]=[C:47]([C:4](=[O:6])[C:3]1[CH:7]=[CH:8][C:9]([F:13])=[C:10]([O:11][CH3:12])[C:2]=1[F:1])[C:48]([O:50][CH2:51][CH3:52])=[O:49]To 376 mg of the 2,4-difluoro-3-methoxybenzoic acid was added 40 mL of tetrahydrofuran. After adding 0.75 ml of triethylamine, 20 mg of N,N-dimethylaminopyridine and 689 mg of 2-methyl-6-nitrobenzoic anhydride to this solution, the mixture was stirred at room temperature. After 2 hours, mixed acid anhydrides were confirmed by TLC, and 430 mg of ethyl N,N-dimethylaminoacrylate was added dropwise thereto. After completion of the dropwise addition, the mixture was stirred for 24 hours. After completion of the reaction, water was added to the reaction mixture, and the separated solution was extracted with ethyl acetate and dried with anhydrous sodium sulfate. After removing the sodium sulfate by filtration, the filtrate was concentration under reduced pressure to obtain 511 mg of a dark brown oily product. The resulting residue was purified by silica gel column chromatography to obtain the title compound.
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