Triethylamine → (S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one

温度

-78 °C

Triethylamine (0.66 mL, 4.75 mmol) was added to a solution of (4-bromo-2-methoxy-phenyl)-acetic acid (1.02 g, 4.162 mmol) in THF (11 mL) in a first round bottom flask under argon atmosphere. The mixture was cooled at −78° C. and pivaloyl chloride (0.513 mL, 4.162 mmol) was added. After stirring for 10 minutes at −78° C., the reaction mixture was warmed to 0° C. and stirred for 30 minutes, then cooled again at −78° C. In second round bottom flask (S)-4-isopropyl-2-oxazolidinone (591.2 mg, 4.577 mmol) was dissolved in THF (20 mL) and cooled to −78° C., and n-BuLi (2.5 M in hexane, 2.0 mL, 4.99 mmol) was added. After stirring for 10 minutes at −78° C., the metallated oxazolidinone mixture in the second flask was added to the mixed anhydride in the first flask at −78° C. The reaction mixture was stirred for 4 hours at 0° C., then at room temperature for 18 hours. A saturated solution of NH4Cl was added, and the mixture was extracted with EtOAc. The combined organic extracts were washed with brine, dried over Na2SO4, filtered and evaporated under reduced pressure. The residue was purified via flash chromatography (hexane/EtOAc, 84/16) to give 1.13 g (77% yield) of (S)-3-[2-(4-bromo-2-methoxy-phenyl)-acetyl]-4-isopropyl-oxazolidin-2-one.

1. temperaturethe reaction mixture was warmed to 0° C.
2. stirringstirred for 30 minutes
3. temperaturecooled again at −78° C
4. temperaturecooled to −78° C.
5. stirringAfter stirring for 10 minutes at −78° C.
6. stirringThe reaction mixture was stirred for 4 hours at 0° C.
7. waitat room temperature for 18 hours
8. extractionthe mixture was extracted with EtOAc
9. washThe combined organic extracts were washed with brine
10. dry with materialdried over Na2SO4
11. filtrationfiltered
12. customevaporated under reduced pressure
13. customThe residue was purified via flash chromatography (hexane/EtOAc, 84/16)

ORDレコード

ord-9f684e4be67b4361b93631980d1af679

出典データセット

uspto-grants-2010_08

DOI

10.6084/m9.figshare.5104873.v1

特許番号

US07776910B2