Sodium Hydroxide → HCID 58537205, compound

HRID 1804482Notes

Reaction equation

HRID 1804482 reaction equation
[F:1][C:2]([C:6]1[C:7]([C:17]([O:19]CC)=[O:18])=[N:8][O:9][C:10]=1[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([F:5])[CH2:3][CH3:4].[OH-].[Na+]>C(O)C>[F:1][C:2]([C:6]1[C:7]([C:17]([OH:19])=[O:18])=[N:8][O:9][C:10]=1[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)([F:5])[CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 58537222HCID 58537222, compound

Product 1

HCID 58537205HCID 58537205, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 4-(1,1-difluoropropyl)-5-phenylisoxazole-3-carboxylate (8.9 mg, 0.030 mmol) and 1N aqueous sodium hydroxide (36 μL, 0.036 mmol) in ethanol (1 mL) was stirred at room temperature for 30 minutes and then concentrated under reduced pressure. The residue was suspended in water (0.5 mL) and acidified with 1N aqueous hydrochloric acid to a pH of ˜3. The aqueous solution was extracted with ethyl acetate (3×2 mL), and the combined organic layers were washed with water (1 mL), washed with brine (1 mL), and dried over anhydrous sodium sulfate. Concentration under reduced pressure afforded 4-(1,1-difluoropropyl)-5-phenylisoxazole-3-carboxylic acid (8.0 mg). The compound had an HPLC ret. time=2.69 min.−Column. YMC COMBISCREEN® ODS-A 4.6×50 mm S-5; Gradient time: 4 min; Flow rate=4 ml/min; Solvent A=10% MeOH−90% Water−0.1% TFA; Solvent B=90% MeOH−10% water−0.1% TFA.

Workup

  1. concentrationconcentrated under reduced pressure
  2. extractionThe aqueous solution was extracted with ethyl acetate (3×2 mL)
  3. washthe combined organic layers were washed with water (1 mL)
  4. washwashed with brine (1 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationConcentration under reduced pressure

Sources & evidence

ORD record
ord-f38afd7d65de470ebb88745daa067884
Source dataset
uspto-grants-2013_01
Patent number
US08354398B2

Reaction notes

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