Water → HCID 86593263, compound

HRID 1610562Notes

Reaction equation

HRID 1610562 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[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:34])([F:33])[CH:30]([F:32])[F:31])[N:23]=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[CH:27]=[CH:26][CH:25]=[C:24]([O:28][C:29]([F:33])([F:34])[CH:30]([F:31])[F:32])[N:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593264HCID 86593264, compound

Product 1

HCID 86593263HCID 86593263, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl (4RS,5SR)-5-(4-fluorophenyl)-2-oxo-4-{[6-(1,1,2,2-tetrafluoroethoxy)pyridin-2-yl]methyl}-1,3-oxazolidine-3-carboxylate (840 mg, 1.72 mmol) in methanol (4 ml) was added a solution (4.12 ml, 2.06 mmol) of 0.5N sodium hydroxide in methanol, and the mixture was stirred at room temperature for 15 min. 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 (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) and recrystallized from ethyl acetate-hexane to give the objective substance (390 mg, 49%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 ml×2)
  2. washThe extract was washed with saturated brine
  3. dry with materialdried (anhydrous magnesium sulfate)
  4. customevaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)
  6. customrecrystallized from ethyl acetate-hexane
  7. customto give the objective substance (390 mg, 49%)

Sources & evidence

ORD record
ord-46b7284a749047bfb3e74d5e85e542c8
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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