Sodium Hydroxide → HCID 22261445, compound

HRID 1610265Notes

Reaction equation

HRID 1610265 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[NH:10][CH:9]2[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:24])[F:23])[CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C.O>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:25])([F:23])[F:24])[CH:16]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:12]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22262077HCID 22262077, compound

Product 1

HCID 22261445HCID 22261445, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

(4RS,5SR)-5-(4-Fluorophenyl)-4-[3-(trifluoromethoxy)benzyl]-1,3-oxazolidin-2-one (4.071 g, 11.46 mmol) and sodium hydroxide (1.83 g, 45.8 mmol) were heated under reflux in ethanol (30 ml)—water (2 ml) for 6 hrs. The reaction solution was diluted with water and extracted twice with ethyl acetate. The collected organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure. The residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=3/1-ethyl acetate) to give the objective substance.

Workup

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel (APS type) column chromatography (hexane/ethyl acetate=3/1-ethyl acetate)
  5. customto give the objective substance

Sources & evidence

ORD record
ord-fe5754cda2b049bb9bbc083346ce21dd
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…