Benzenepropanoic acid → Benzeneacetamide, a-methyl-

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.

1. stirringstirred overnight
2. customthe layers were separated
3. extractionThe aqueous layer was extracted with ethyl acetate
4. washthe combined organic layer was washed with saturated aqueous sodium chloride
5. dry with materialdried over anhydrous magnesium sulfate
6. filtrationfiltered
7. concentrationThe filtrate was concentrated under reduced pressure
8. customthe resulting residue was purified by preparative thin layer chromatography (chloroform:methanol:28% aqueous ammonia=20:1:0.1)

ORD record

ord-2b1ddda9bb4948b5b265ae583d60384c

Source dataset

uspto-grants-2015_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09139609B2