Sodium Hydroxide → HCID 22261464, compound

HRID 1610539Notes

Reaction equation

HRID 1610539 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([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:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=2)[CH:5]=[CH:6][CH:7]=1.[OH-].[Na+]>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=1)[CH:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261713HCID 22261713, compound

Product 1

HCID 22261464HCID 22261464, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(3-fluorophenyl)-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (3.30 g, 8.52 mmol) in ethanol (12 ml) was added 8N aqueous sodium hydroxide solution (5.3 ml, 42 mmol), and the mixture was heated under reflux for 5 hrs. The reaction solutions was concentrated, diluted with water (100 ml), and extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from diisopropyl ether-hexane to give the objective substance (2.60 g, 84%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. concentrationThe reaction solutions was concentrated
  4. additiondiluted with water (100 ml)
  5. extractionextracted with ethyl acetate (100 ml×2)
  6. washThe extract was washed with saturated brine
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. customevaporated under reduced pressure
  9. customThe residue was recrystallized from diisopropyl ether-hexane
  10. customto give the objective substance (2.60 g, 84%)

Sources & evidence

ORD record
ord-9356485c9c0149a3b0f484834bdcfa28
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…