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

HRID 1361065Notes

Reaction equation

HRID 1361065 reaction equation
[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[NH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li]CCCC.[F:19][C:20]1[CH:30]=[CH:29][C:23]([O:24][CH2:25][C:26](Cl)=[O:27])=[CH:22][C:21]=1[CH3:31].[NH4+].[Cl-]>C1COCC1>[CH2:1]([C@H:8]1[CH2:12][O:11][C:10](=[O:13])[N:9]1[C:26](=[O:27])[CH2:25][O:24][C:23]1[CH:29]=[CH:30][C:20]([F:19])=[C:21]([CH3:31])[CH:22]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 736225(S)-4-Benzyl-2-oxazolidinoneHCID 597752042-(4-Fluoro-3-methylphenoxy)acetyl chlorideHCID 178418339Butyllithium

Product 1

HCID 59775212(S)-4-Benzyl-3-(2-(4-fluoro-3-methylphenoxy)acetyl)oxazolidin-2-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-70 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-00a6118277094680bb606e0a033a2f58
Source dataset
uspto-grants-2011_02
Patent number
US07879911B2

Reaction notes

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