Water → HCID 15463514, compound

HRID 430789Notes

Reaction equation

HRID 430789 reaction equation
[CH2:1]([S:8]([NH:11][CH2:12][CH2:13][C:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:17]=2[O:16][CH:15]=1)(=[O:10])=[O:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C=O)C>[CH2:1]([S:8]([N:11]([CH2:12][CH2:13][C:14]1[C:18]2[CH:19]=[CH:20][CH:21]=[C:22]([O:23][CH2:24][C:25]([O:27][CH3:28])=[O:26])[C:17]=2[O:16][CH:15]=1)[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=[O:9])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 54102406HCID 54102406, compound

Product 1

HCID 15463514HCID 15463514, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl (3-(2-(benzylsulfonylamino)ethyl)benzofuran-7-yloxy)acetate (143 mg) was dissolved in DMF (3 ml), and potassium carbonate (49 mg) and benzyl bromide (0.13 ml) were added to the obtained solution, followed by stirring the resulting mixture at room temperature for 27 hours and then at 50° C. for 14.5 hours. The reaction solution was poured into water layer (50 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with 1N hydrochloric acid and with saturated brine, followed by drying over 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: hexane/ethyl acetate=2/1-1/1) using silica gel to obtain the desired compound (100 mg, yield: 57%).

Workup

  1. waitat 50° C. for 14.5 hours
  2. extractionthe resultant was extracted twice with ethyl acetate (20 ml)
  3. washwashed with 1N hydrochloric acid and with saturated brine
  4. dry with materialby drying over sodium sulfate
  5. customAfter removing the sodium sulfate
  6. filtrationby filtration
  7. customthe solvent was removed under reduced pressure
  8. customthe residue was purified by column chromatography (solvent: hexane/ethyl acetate=2/1-1/1)

Sources & evidence

ORD record
ord-71f1c287414a4e6b8ca20209e9abe1ea
Source dataset
uspto-grants-2001_11
Patent number
US06323235B1

Reaction notes

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