Sodium Hydroxide → HCID 22261540, compound

HRID 1610691Notes

Reaction equation

HRID 1610691 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH:8]([OH:28])[CH:9]([CH2:15][C:16]2[O:20][N:19]=[C:18]([O:21][C:22]([F:27])([F:26])[CH:23]([F:25])[F:24])[CH:17]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8]([OH:28])[CH:9]([CH2:15][C:16]2[O:20][N:19]=[C:18]([O:21][C:22]([F:26])([F:27])[CH:23]([F:25])[F:24])[CH:17]=2)[C:10]([OH:12])=[O:11])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86593294HCID 86593294, compound

Product 1

HCID 22261540HCID 22261540, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of ethyl (2RS,3SR)-3-(4-fluorophenyl)-3-hydroxy-2-[[3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methyl]propionate (1.402 g, 3.425 mmol) in methanol (30 ml) was added 1N aqueous sodium hydroxide solution (6.85 ml, 6.85 mmol), and the mixture was stirred at room temperature for 2 hrs. The reaction solution was concentrated and diluted with water. The reaction solution was acidified with 1N hydrochloric acid, and extracted twice with ethyl acetate. The recovered organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated under reduced pressure to give a crude product of (2RS,3SR)-3-(4-fluorophenyl)-3-hydroxy-2-[[3-(1,1,2,2-tetrafluoroethoxy)isoxazol-5-yl]methyl]propionic acid as a colorless liquid.

Workup

  1. concentrationThe reaction solution was concentrated
  2. additiondiluted with water
  3. extractionextracted twice with ethyl acetate
  4. dry with materialThe recovered organic layer was dried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-392c0800ab1946d6a6e212e77d73268f
Source dataset
uspto-grants-2006_01
Patent number
US06982348B2

Reaction notes

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