Water → HCID 67546842, compound

HRID 2356718Notes

Reaction equation

HRID 2356718 reaction equation
[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]([NH:8][CH:9]([C:18]2[S:19][CH:20]=[CH:21][CH:22]=2)[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=O)=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.O.C(=O)([O-])O.[Na+]>CN(C)C=O>[F:1][C:2]1[CH:24]=[CH:23][C:5]([C:6]2[O:17][C:10]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])=[C:9]([C:18]3[S:19][CH:20]=[CH:21][CH:22]=3)[N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 67548710HCID 67548710, compound

Product 1

HCID 67546842HCID 67546842, compoundYield 28.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-(4-fluorobenzoylamino)-4-(2-thienyl)-3-ketobutyrate (349 mg), and phosphorus oxychloride (0.12 ml) in N,N-dimethylformamide (5 ml) was stirred at room temperature for 2.5 hours. The reaction mixture was poured into water, neutralized with a saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was removed under reduced pressure. The resulting residue was purified by silica gel flush column chromatography (solvent: hexane:ethyl acetate=20:1) to obtain ethyl 2-(4-fluorophenyl)-4-(2-thienyl)oxazol-5-ylacetate (95 mg) as pale yellowish powder.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by silica gel
  6. customflush column chromatography (solvent: hexane:ethyl acetate=20:1)

Sources & evidence

ORD record
ord-ecf3fa75735d4b55ac50eae15be98977
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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