Sodium Hydroxide → HCID 22262028, compound

HRID 1610670Notes

Reaction equation

HRID 1610670 reaction equation
[Br: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:27])([F:26])[CH:23]([F:25])[F:24])[CH:16]=2)=[CH:4][CH:3]=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:5]1[CH:6]=[CH:7][C:2]([Br:1])=[CH:3][CH:4]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261543HCID 22261543, compound

Product 1

HCID 22262028HCID 22262028, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-bromophenyl)-4-[3-(1,1,2,2-tetrafluoroethoxy)benzyl]-1,3-oxazolidin-2-one (14.0 g, 31.2 mmol) in ethanol (50 ml) was added 8N aqueous sodium hydroxide solution (15.6 ml, 125 mmol) and the mixture was heated under reflux for 2 hrs. The reaction solution was concentrated under reduced pressure, and water (200 ml) was added. The mixture was extracted with ethyl acetate (200 ml×2). The extract was washed with water, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was crystallized from hexane-diethyl ether to give the objective substance (12.8 g, 97%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 2 hrs
  3. concentrationThe reaction solution was concentrated under reduced pressure, and water (200 ml)
  4. additionwas added
  5. extractionThe mixture was extracted with ethyl acetate (200 ml×2)
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customevaporated under reduced pressure
  9. customThe residue was crystallized from hexane-diethyl ether
  10. customto give the objective substance (12.8 g, 97%)

Sources & evidence

ORD record
ord-87618fc64849450aa7dea3fff6ae2412
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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