Water → HCID 67546985, compound

HRID 2356727Notes

Reaction equation

HRID 2356727 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7](=[O:23])[CH:8]([NH:13][C:14](=O)[C:15]2[CH:20]=[CH:19][C:18]([F:21])=[CH:17][CH:16]=2)[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1.P(Cl)(Cl)(Cl)=O.O>CN(C)C=O>[Cl:1][C:2]1[S:6][C:5]([C:7]2[O:23][C:14]([C:15]3[CH:16]=[CH:17][C:18]([F:21])=[CH:19][CH:20]=3)=[N:13][C:8]=2[C:9]([O:11][CH3:12])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24813Phosphorus oxychlorideHCID 67547784HCID 67547784, compound

Product 1

HCID 67546985HCID 67546985, compoundYield 40.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of methyl 3-(5-chlorothiophen-2-yl)-2-(4-fluorobenzoylamino)-3-oxopropionate (7.25 g) in N,N-dimethyl-formamide (80 ml) was added dropwise phosphorus oxychloride (5.7 ml) under ice-cooling, and the mixture was then stirred at room temperature for 3 days. After cooling, water was added to the reaction mixture and the mixture was 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 column chromatography (solvent: hexane:ethyl acetate=100:1), and then, triturated with diethyl ether-hexane to obtain methyl 5-(5-chloro-thiophen-2-yl)-2-(4-fluorophenyl)oxazol-4-carboxylate (2.8 g) as colorless powder.

Workup

  1. temperaturecooling
  2. temperatureAfter cooling
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with water and brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (solvent: hexane:ethyl acetate=100:1)
  8. customtriturated with diethyl ether-hexane

Sources & evidence

ORD record
ord-9006ada0707e4e9ea379c953c68f5e4a
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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