Water → HCID 22261753, compound

HRID 1610614Notes

Reaction equation

HRID 1610614 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]([S:21][C:22]([F:25])([F:24])[F:23])[CH:16]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>C(O)C>[NH2:10][CH:9]([CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[C:17]([S:21][C:22]([F:25])([F:24])[F:23])[CH:16]=1)[CH:8]([C:5]1[CH:6]=[CH:7][C:2]([F:1])=[CH:3][CH:4]=1)[OH:12]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 22261563HCID 22261563, compound

Product 1

HCID 22261753HCID 22261753, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of (4RS,5SR)-5-(4-fluorophenyl)-4-{3-[(trifluoromethyl)thio]benzyl}-1,3-oxazolidin-2-one (1.30 g, 3.50 mmol) in ethanol (3 ml) was added 8N aqueous sodium hydroxide solution (1.31 ml,10.5 mmol), and the mixture was stirred at 80° C. for 4 hrs. To the reaction solution was added water (20 ml), and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with water and saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure to give the objective substance (0.8 g, 77%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  2. washThe extract was washed with water and saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customto give the objective substance (0.8 g, 77%)

Sources & evidence

ORD record
ord-c5f423999955486a868da9b2ad0afe80
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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