Trifluoroacetic acid → HCID 17856251, compound

To a solution of 500 mg of 2,2,2-trifluoro-N-[2-(2-hydroxy-4-isopropylphenyl)-2-oxoethyl]acetamide in 2.63 mL of trifluoroacetic acid was added 0.94 mL of triethylsilane. After being stirred at room temperature for 13 hours, the reaction mixture was concentrated and dried thoroughly. The obtained residue and 382 mg of potassium carbonate were suspended in 10 mL of N,N-dimethylformamide, and 0.288 mL of ethyl bromoacetate was added to the stirred mixture under ice-cooling. The mixture was stirred at room temperature for 15 hours, and to the reaction mixture was added water. After the mixture was extracted with ethyl acetate, the organic layer was washed successively with water and brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane) to give 535 mg of ethyl[5-isopropyl-2-[2-(2,2,2-trifluoroacetylamino)ethyl]phenoxy]acetate.

1. concentrationthe reaction mixture was concentrated
2. customdried thoroughly
3. addition0.288 mL of ethyl bromoacetate was added to the stirred mixture under ice-
4. temperaturecooling
5. stirringThe mixture was stirred at room temperature for 15 hours
6. additionto the reaction mixture was added water
7. extractionAfter the mixture was extracted with ethyl acetate
8. washthe organic layer was washed successively with water and brine
9. dry with materialdried over anhydrous magnesium sulfate
10. customThe solvent was removed under reduced pressure
11. customthe obtained residue was purified by column chromatography on silica gel (eluent: ethyl acetate-hexane)

ORD record

ord-7b0d3d42078a42ec9e60c8714748c77e

Source dataset

uspto-grants-2009_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07563822B2