Ammonium Chloride → (S)-4-Benzyl-3-(2-(4-fluoro-3-methylphenoxy)acetyl)oxazolidin-2-one

온도

-70 °C

To the solution of (S)-4-Benzyl-2-oxazolidinone (857 mg, 4.8 mmol) in anhydrous 30 mL THF at −70° C. was slowly added n-BuLi (3.0 mL, 4.8 mmol, 1.6 M in hexane) over 15 minutes. The reaction mixture was stirred for 30 min at −70° C. and to it was slowly added a solution of 2-(4-fluoro-3-methylphenoxy)acetyl chloride crude solution in 4 mL THF. The resulting mixture was stirred at −70° C. for 2 h and the temperature was slowly raised over a period of 1 h. The mixture was poured into 30 mL saturated NH4Cl and extracted with ethyl acetate (3×40 mL). The combined organic layers were washed with brine (2×30 mL) and dried over Na2SO4. The solvent was removed under reduced pressure and the product isolated by Flash column chromatography eluting with 0% to 50% ethyl acetate/hexane to give 1.5 g of the title compound as a light yellow oil.

1. customat −70° C.
2. customover 15 minutes
3. stirringThe resulting mixture was stirred at −70° C. for 2 h
4. temperaturethe temperature was slowly raised over a period of 1 h
5. extractionextracted with ethyl acetate (3×40 mL)
6. washThe combined organic layers were washed with brine (2×30 mL)
7. dry with materialdried over Na2SO4
8. customThe solvent was removed under reduced pressure
9. customthe product isolated by Flash column chromatography
10. washeluting with 0% to 50% ethyl acetate/hexane

ORD 기록

ord-00a6118277094680bb606e0a033a2f58

출처 데이터셋

uspto-grants-2011_02

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US07879911B2