Sodium Hydroxide → HCID 22262254, compound

HRID 1610647Notes

Reaction equation

HRID 1610647 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][CH:22]([CH3:24])[CH3:23])[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][CH:22]([CH3:24])[CH3:23])[CH:16]=1)[CH:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)[OH:12]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261652(4RS,5SR)-5-(4-fluorophenyl)-4-[3-(isopropyloxy)benzyl]-1,3-oxazolidin-2-one

Product 1

HCID 22262254HCID 22262254, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-5-(4-fluorophenyl)-4-[3-(isopropyloxy)benzyl]-1,3-oxazolidin-2-one (5.85 g, 17.8 mmol) in ethanol (30 ml) was added 8N aqueous sodium hydroxide solution (8.9 ml, 71.0 mmol), and the mixture was heated under reflux for 5 hrs. The reaction solution-was concentrated under reduced pressure. To the solution was added water (100 ml) and the mixture was extracted with ethyl acetate (100 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 (5.0 g, 93%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hrs
  3. concentrationThe reaction solution-was concentrated under reduced pressure
  4. additionTo the solution was added water (100 ml)
  5. extractionthe mixture was extracted with ethyl acetate (100 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 (5.0 g, 93%)

Sources & evidence

ORD record
ord-0f3dc0db0e454fe0be979ce657e85172
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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