Methanol → HCID 178515650, compound

HRID 384106Notes

Reaction equation

HRID 384106 reaction equation
[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:24][N:23]=[C:22](CC(C)(C)C([O-])=O)[CH:21]=4)=[CH:16][CH:15]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[OH:33]>CO.[OH-].[K+]>[C:1]1([C:7]2[O:11][N:10]=[C:9]([CH2:12][O:13][C:14]3[CH:19]=[CH:18][C:17]([C:20]4[O:24][N:23]=[C:22]([OH:33])[CH:21]=4)=[CH:16][CH:15]=3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 86641938HCID 86641938, compound

Product 1

HCID 178515650HCID 178515650, compound

Reagents, catalysts & solvents 1

HCID 23689386Potassium hydroxide methanolSolvent

Procedure

To a solution of 5-(4-((5-phenylisoxazol-3-yl)methoxy)phenyl)isoxazol-3-ylpivalate (21 mg) in methanol (2 ml), 0.4 ml of 5M potassium hydroxide methanol solution was added, and the reaction solution was stirred at room temperature for 1 hour. The reaction solution was neutralized, then extracted with chloroform, and dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the residue obtained was purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid). The solvent of the resultant fraction was distilled off under reduced pressure to afford the title compound as a white solid.

Workup

  1. extractionextracted with chloroform
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThe solvent was distilled off under reduced pressure
  4. customthe residue obtained
  5. customwas purified through reversed phase medium pressure liquid chromatography (ODS-AS-360-CC (by YMC), mobile phase: water-acetonitrile-0.1% trifluoroacetic acid)
  6. distillationThe solvent of the resultant fraction was distilled off under reduced pressure

Sources & evidence

ORD record
ord-9d787b8c5f024054bc92839a9a75cdcf
Source dataset
uspto-grants-2013_02
Patent number
US08367708B2

Reaction notes

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