Water → HCID 86593284, compound

HRID 1610638Notes

Reaction equation

HRID 1610638 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]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:30])=[O:29])[CH: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])([CH3:19])[CH3:20])[CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([S:28]([C:31]([F:34])([F:33])[F:32])(=[O:29])=[O:30])[CH:23]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 86593285HCID 86593285, compound

Product 1

HCID 86593284HCID 86593284, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a solution of tert-butyl (4RS,5SR)-5-(4-fluorophenyl)-2-oxo-4-{3-[(trifluoromethyl)sulfonyl]benzyl}-1,3-oxazolidine-3-carboxylate (0.90 g, 1.79 mmol) in methanol (10 ml) was added a solution of 0.5N sodium hydroxide in methanol (10.8 ml, 5.40 mmol), and the mixture was stirred at room temperature for 30 min. To the reaction solution was added water (50 ml), and the mixture was extracted with ethyl acetate (100 ml×2). The extract was washed with saturated brine, dried (anhydrous magnesium sulfate) and evaporated under reduced pressure. The residue was recrystallized from ethyl acetate-hexane to give the objective substance (0.72 g, 84%).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (100 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 recrystallized from ethyl acetate-hexane
  6. customto give the objective substance (0.72 g, 84%)

Sources & evidence

ORD record
ord-92efc35661f3443f84379ef002597dd2
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

Loading…