Sodium Hydroxide → HCID 22262206, compound

HRID 1610654Notes

Reaction equation

HRID 1610654 reaction equation
[C:1]([O:5][C:6]1[CH:7]=[C:8]([CH:23]=[CH:24][CH:25]=1)[CH2:9][CH:10]1[CH:14]([C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[O:13]C(=O)[NH:11]1)([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>C(O)C>[NH2:11][CH:10]([CH2:9][C:8]1[CH:23]=[CH:24][CH:25]=[C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])[CH:7]=1)[CH:14]([C:15]1[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=1)[OH:13]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 22261968HCID 22261968, compound

Product 1

HCID 22262206HCID 22262206, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of (4RS,5SR)-4-[3-(tert-butyloxy)benzyl]-5-(4-fluorophenyl)-1,3-oxazolidin-2-one (6.6 g, 19.2 mmol) in ethanol (30 ml) was added 8N aqueous sodium hydroxide solution (9.6 ml, 76.9 mmol), and the mixture was heated under reflux for 4 hrs. The reaction solution was concentrated under reduced pressure. Water (150 ml) was added, and the mixture was extracted with ethyl acetate (200 ml). 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 (5.86 g, 96%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 hrs
  3. concentrationThe reaction solution was concentrated under reduced pressure
  4. additionWater (150 ml) was added
  5. extractionthe mixture was extracted with ethyl acetate (200 ml)
  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 (5.86 g, 96%)

Sources & evidence

ORD record
ord-4d5aa33b2d35457c8f00652d52e7f2f2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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