Water → HCID 86593250, compound

HRID 1610433Notes

Reaction equation

HRID 1610433 reaction equation
O=C1[N:6]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])[CH:5]([CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=2)[CH:4]([C:25]2[CH:30]=[CH:29][N:28]=[CH:27][CH:26]=2)[O:3]1.[OH-].[Na+].O>CO>[OH:3][CH:4]([C:25]1[CH:26]=[CH:27][N:28]=[CH:29][CH:30]=1)[CH:5]([NH:6][C:7](=[O:8])[O:9][C:10]([CH3:12])([CH3:13])[CH3:11])[CH2:14][C:15]1[CH:20]=[CH:19][C:18]([C:21]([F:24])([F:23])[F:22])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593249HCID 86593249, compound

Product 1

HCID 86593250HCID 86593250, compoundYield 83.6%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1,1-dimethylethyl (4RS,5SR)-2-oxo-5-(4-pyridyl)-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidine-3-carboxylate (500 mg, 1.18 mmol) in methanol (2.8 ml) was added 0.5N sodium hydroxide (2.8 ml, 1.40 mmol), and the mixture was stirred at room temperature for 1 hr. To the reaction solution was added water (20 ml), and the mixture was extracted with ethyl acetate (20 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 (391 mg, 83%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (20 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-764e7486b165426c817bf6fe090f02b7
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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