HCID 22926962, compound → HCID 57719651, compound

HRID 1985410Notes

Reaction equation

HRID 1985410 reaction equation
[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]1[CH2:9][CH2:8][O:7][C:6]1=[O:10].[NH2:16][C:17]1[CH:18]=[C:19]([CH2:23][CH:24]([O:30][CH:31]([CH3:33])[CH3:32])[C:25]([O:27]CC)=[O:26])[CH:20]=[CH:21][CH:22]=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:14]=[C:13]([Cl:15])[CH:12]=[CH:11][C:3]=1[O:4][CH:5]([CH2:9][CH2:8][OH:7])[C:6]([NH:16][C:17]1[CH:18]=[C:19]([CH2:23][CH:24]([O:30][CH:31]([CH3:33])[CH3:32])[C:25]([OH:27])=[O:26])[CH:20]=[CH:21][CH:22]=1)=[O:10]

Participants

4

Reactant 2

HCID 22926962HCID 22926962, compoundHCID 57719572HCID 57719572, compound

Product 1

HCID 57719651HCID 57719651, compoundYield 17.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

20 mg of 3-(2,4-Dichlorophenoxy)dihydrofuran-2-one and 30 mg of ethyl 3-(3-aminophenyl)-2-isopropoxypropanoate were dissolved in 1 ml of toluene, and the solution was heated under reflux for 8 hours. After removing the solvent under a stream of nitrogen, the residue was dissolved in 0.6 ml of ethanol, and 0.12 ml of 5N sodium hydroxide was added thereto, and the mixture was stirred at room temperature for 1 hour. The reaction solution was diluted with 2 ml of water and 0.14 ml of 5N hydrochloric acid, and extracted with ethyl acetate. The organic layer was collected, and the solvent was removed under a stream of nitrogen. The residue was purified by HPLC using a reverse-phase column and a water-acetonitrile-trifluoroacetic acid elution solvent, to give 6.8 mg of the title compound.

Workup

  1. temperaturethe solution was heated
  2. temperatureunder reflux for 8 hours
  3. customAfter removing the solvent under a stream of nitrogen
  4. dissolutionthe residue was dissolved in 0.6 ml of ethanol
  5. addition0.12 ml of 5N sodium hydroxide was added
  6. additionThe reaction solution was diluted with 2 ml of water and 0.14 ml of 5N hydrochloric acid
  7. extractionextracted with ethyl acetate
  8. customThe organic layer was collected
  9. customthe solvent was removed under a stream of nitrogen
  10. customThe residue was purified by HPLC
  11. washa water-acetonitrile-trifluoroacetic acid elution solvent

Sources & evidence

ORD record
ord-20acb914d5d0404caae164ebd418bb80
Source dataset
uspto-grants-2009_06
Patent number
US07544835B2

Reaction notes

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