Water → 4-Hexyl-3-[(4-methoxycarbonylphenyl)methyl]aminobenzoic acid morpholide

Reaction equation

[NH2:1][C:2]1[CH:3]=[C:4]([CH:13]=[CH:14][C:15]=1[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])[C:5]([N:7]1[CH2:12][CH2:11][O:10][CH2:9][CH2:8]1)=[O:6].[CH3:22][O:23][C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=O)=[CH:28][CH:27]=1)=[O:25].O>C(O)(=O)C>[CH2:16]([C:15]1[CH:14]=[CH:13][C:4]([C:5]([N:7]2[CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)=[O:6])=[CH:3][C:2]=1[NH:1][CH2:30][C:29]1[CH:28]=[CH:27][C:26]([C:24]([O:23][CH3:22])=[O:25])=[CH:33][CH:32]=1)[CH2:17][CH2:18][CH2:19][CH2:20][CH3:21]

Participants

Procedure

The compound ([5]-(55)-75) (600 mg) prepared in Example 63 was dissolved in acetic acid (6.0 ml). Then, 4-methoxycarbonylbenzaldehyde (373 mg) was added. The mixture was stirred at room temperature for 4 hours. Then, boranediethylamine complex (146 mg) was added to the solution. The mixture was stirred at room temperature for 30 minutes. After the reaction was completed, water was added to the solution. The solution was extracted with ethyl acetate, washed with distilled water, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (Kieselgel 60=30 g, hexane/ethyl acetate=1/1) to obtain the above-captioned compound ([5]-(57)-75') (841 mg) as a white solid.