Water → HCID 91393564, compound

HRID 1610450Notes

Reaction equation

HRID 1610450 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([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[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:30])[F:29])=[CH:24][CH:23]=2)[CH:5]=[CH:4][CH:3]=1.CO.[OH-].[Na+].O>CO>[Cl:1][C:2]1[N:7]=[C:6]([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[CH:27]=[CH:26][C:25]([C:28]([F:31])([F:29])[F:30])=[CH:24][CH:23]=2)[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 22262045HCID 22262045, compoundHCID 23721981Sodium hydroxide methanol

Product 1

HCID 91393564HCID 91393564, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To 1,1-dimethylethyl(4RS,5RS)-5-(6-chloro-2-pyridyl)-2-oxo-4-((4-(trifluoromethyl)phenyl)methyl)-1,3-oxazolidine-3-carboxylate (677 mg, 1.46 mmol) in methanol (3.5 ml) was added 0.5N sodium hydroxide methanol solution (3.5 ml, 1.75 mmol) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. To the reaction solution was added water (50 ml), 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 purified by silica gel column chromatography (ethyl acetate) and recrystallized from diisopropyl ether-hexane to give the title compound (550 mg, 57%).

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 purified by silica gel column chromatography (ethyl acetate)
  7. customrecrystallized from diisopropyl ether-hexane

Sources & evidence

ORD record
ord-61ad9853d1b942b8b71d7255bed6cd71
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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