Triethylamine → HCID 67547595, compound

HRID 2356757Notes

Reaction equation

HRID 2356757 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]3[O:11]C(=O)[C:13]([CH3:19])([C:15]([O:17]C)=O)[N:14]=3)[CH:8]=[CH:9][C:2]1=2.[CH:21]1[S:25][CH:24]=[CH:23][C:22]=1C(Cl)=O.C(N(CC)CC)C.[C:36]([O:39][CH2:40]C)(=[O:38])C>>[O:1]1[CH:5]=[CH:4][C:3]2[CH:6]=[C:7]([C:10]([NH:14][CH:13]([C:15]([C:23]3[CH:22]=[CH:21][S:25][CH:24]=3)=[O:17])[CH2:19][C:36]([O:39][CH3:40])=[O:38])=[O:11])[CH:8]=[CH:9][C:2]1=2

Participants

5

Reactant 4

HCID 8471TriethylamineHCID 8857Ethyl Acetate2×HCID 27763773-Thenoyl chlorideHCID 67547607HCID 67547607, compound

Product 1

HCID 67547595HCID 67547595, compound

Procedure

To a mixture of 2-(5-benzo[b]furyl)-4-methoxycarbonyl-methyl-5-oxo-2-oxazoline (410 mg) and 3-thenoyl chloride (242 mg) in ethyl acetate (8 ml) was added triethyl amine (0.23 ml) under ice-cooling, and the mixture was stirred at room temperature for 0.5 hour. Ethyl acetate was added to the mixture, the mixture was filtered and the resulting filtrate was concentrated under reduced pressure. A mixture of the resulting residue and pyridine (3.6 ml) was stirred at room temperature for 10 minutes followed by stirring at 60° C. for 2 hours. Then, acetic acid (1.35 ml) was added to the mixture and the resulting mixture was stirred at 80° C. for 1.5 hours. After cooling, to the reaction mixture were added water and ethyl acetate, the organic layer was collected, washed successively with a 10% aqueous hydrochloric acid solution, a saturated aqueous sodium hydrogen carbonate solution 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=5:1) to obtain methyl 3-(5-benzo[b]furoylamino)-4-(3-thienyl)-4-oxobutyrate (253 mg) as colorless powder.

Workup

  1. temperaturecooling
  2. filtrationthe mixture was filtered
  3. concentrationthe resulting filtrate was concentrated under reduced pressure
  4. additionA mixture of the resulting residue and pyridine (3.6 ml)
  5. stirringwas stirred at room temperature for 10 minutes
  6. stirringby stirring at 60° C. for 2 hours
  7. additionThen, acetic acid (1.35 ml) was added to the mixture
  8. stirringthe resulting mixture was stirred at 80° C. for 1.5 hours
  9. temperatureAfter cooling, to the reaction mixture
  10. additionwere added water and ethyl acetate
  11. customthe organic layer was collected
  12. washwashed successively with a 10% aqueous hydrochloric acid solution
  13. dry with materiala saturated aqueous sodium hydrogen carbonate solution and brine, dried over anhydrous sodium sulfate
  14. customthe solvent was removed under reduced pressure
  15. customThe resulting residue was purified by silica gel column chromatography (solvent: hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-548712020b54489ca55ef26ff296c9ef
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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