Water → HCID 86593233, compound

HRID 1610333Notes

Reaction equation

HRID 1610333 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]2[O:12]C(=O)[N:10]([C:14]([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15])[CH:9]2[CH2:21][C:22]2[O:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O>CO>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:12])[CH:9]([NH:10][C:14](=[O:15])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:21][C:22]2[O:23][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:25][CH:26]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593232HCID 86593232, compound

Product 1

HCID 86593233HCID 86593233, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 1,1-dimethylethyl (4RS,5SR)-5-(4-fluorophenyl)-2-oxo-4-((5-(trifluoromethyl)-2-furanyl)methyl)-1,3-oxazolidine-3-carboxylate (1.91 g, 4.45 mmol) in methanol (10.7 ml) was added a methanol solution (10.7 ml, 5.35 mmol) of 0.5N sodium hydroxide under ice-cooling and the mixture was stirred at room temperature for 10 min. Water (50 ml) was added to the reaction solution and the mixture was extracted with ethyl acetate (50 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the title compound (1.79 g, 100%).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated under reduced pressure
  6. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-531c11a515804c129dd5b0fe659703a2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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