Methanol → HCID 53784183, compound

HRID 430786Notes

Reaction equation

HRID 430786 reaction equation
[C:1]([O:4][C:5]1[C:13]2[O:12][CH:11]=[C:10]([CH2:14][NH:15][C:16](=[O:18])[CH3:17])[C:9]=2[CH:8]=[CH:7][CH:6]=1)(=O)[CH3:2].[C:19](=O)([O-])[O-:20].[K+].[K+].C[OH:26]>>[C:16]([NH:15][CH2:14][C:10]1[C:9]2[CH:8]=[CH:7][CH:6]=[C:5]([O:4][CH2:1][C:2]([O:20][CH3:19])=[O:26])[C:13]=2[O:12][CH:11]=1)(=[O:18])[CH3:17]

Participants

4

Reactant 3

HCID 887MethanolHCID 11430Potassium CarbonateHCID 18351826HCID 18351826, compound

Product 1

HCID 53784183HCID 53784183, compoundYield 78%

Procedure

7-acetoxy-3-((acetylamino)methyl)benzofuran (258 mg) and potassium carbonate (82 mg) were added to methanol (5 ml) and the obtained mixture was stirred at room temperature for 1 hour. After removing methanol under reduced pressure, DMF (5 ml) and methyl bromoacetate (0.15 ml) were added to the residue, followed by stirring the resultant for 18 hours. The reaction solution was poured into water layer (30 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturated brine, followed by drying over anhydrous sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: chloroform/methanol=95/5) using silica gel to obtain the desired compound (227 mg, yield: 78%).

Workup

  1. customAfter removing methanol under reduced pressure, DMF (5 ml) and methyl bromoacetate (0.15 ml)
  2. additionwere added to the residue
  3. stirringby stirring the resultant for 18 hours
  4. additionThe reaction solution was poured into water layer (30 ml)
  5. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  6. washwashed with saturated brine
  7. dry with materialby drying over anhydrous sodium sulfate
  8. customAfter removing the sodium sulfate
  9. filtrationby filtration
  10. customthe solvent was removed under reduced pressure
  11. customthe residue was purified by column chromatography (solvent: chloroform/methanol=95/5)

Sources & evidence

ORD record
ord-5ba3f932df8c4046a9eb55b2e5c03145
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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