Hydrochloric Acid → HCID 67546961, compound

HRID 2356719Notes

Reaction equation

HRID 2356719 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:18][C:19]([O:21]CC)=[O:20])=[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:4][CH:3]=1.[OH-].[Na+:25].Cl>O1CCCC1.C(O)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]([CH2:18][C:19]([O-:21])=[O:20])=[C:11]([C:13]3[S:14][CH:15]=[CH:16][CH:17]=3)[N:12]=2)=[CH:4][CH:3]=1.[Na+:25]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67546842HCID 67546842, compound

Product 1

HCID 67546961HCID 67546961, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of ethyl 2-(4-fluorophenyl)-4-(2-thienyl)-oxazol-5-ylacetate (94 mg) in tetrahydrofuran (3 ml) and ethanol (3 ml) was added 1N aqueous sodium hydroxide solution (1 ml) and the mixture was stirred at room temperature for one hour. To the reaction mixture was added 10% hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was dissolved in methanol (5 ml), 0.5M sodium methoxide (556 μl, methanol solution) was added to the solution and the solvent was removed under reduced pressure to obtain sodium 2-(4-fluorophenyl)-4-(2-thienyl)oxazol-5-ylacetate (90 mg) as pale brownish powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. dissolutionThe resulting residue was dissolved in methanol (5 ml)
  6. addition0.5M sodium methoxide (556 μl, methanol solution) was added to the solution
  7. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-46ce66cefd7948008f9aa223318492bf
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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