[C:1]1([CH2:7][CH2:8]C(O)=O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.ClC([O:15][CH2:16]C(C)C)=O.O.[NH2:21]N.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C.C(N(CC)CC)C>[C:1]1([CH:7]([CH3:8])[C:16]([NH2:21])=[O:15])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1
3-Phenylpropionic acid (12 mg) was dissolved in tetrahydrofuran (2 ml), and triethylamine (12 μl) and isobutyl chloroformate (11 μl) were added to the solution under ice cooling. The reaction mixture was stirred at the same temperature for 1 hour, and then a solution of the compound obtained in Example 190, (1) in tetrahydrofuran (1 ml) was slowly added dropwise to the reaction mixture at −78° C. The reaction mixture was gradually warmed to room temperature, and stirred overnight. Then, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added to the reaction mixture, and the layers were separated. The aqueous layer was extracted with ethyl acetate, and the combined organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate, and filtered. The filtrate was concentrated under reduced pressure, and the resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=20:1:0.1) to obtain a phenylpropionamide compound (22 mg). (2) By using the compound obtained in (1) mentioned above (22 mg) as a starting material, the compound shown in Table 5 (15 mg) was obtained in the same manners as those of Example 4, (6) and Example 11.
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