Potassium Carbonate → HCID 57742155, compound

HRID 660287Notes

Reaction equation

HRID 660287 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[CH:11]=[CH:10][C:9]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:8][C:7]=1[OH:19])=[O:4].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.O>[O:4]=[C:3]1[CH2:2][O:19][C:7]2[CH:8]=[C:9]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:10]=[CH:11][C:6]=2[NH:5]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 57742180HCID 57742180, compound

Product 1

HCID 57742155HCID 57742155, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A solution of ethyl 2-(4-(2-chloroacetamido)-3-hydroxyphenyl)propanoate (110 mg, 0.385 mmol) in acetone (10 mL) was added potassium carbonate (61 mg). the reaction mixture was refluxed for 3 hrs then cooled to room temperature. The mixture was diluted with H2O and extracted with EtOAc. The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel using EtOAc:hexanes (1:2) as eluent.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hrs
  2. extractionextracted with EtOAc
  3. dry with materialThe organic layer was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-f9b4c14b10954a1d9b818652dd0eacec
Source dataset
uspto-grants-2011_12
Patent number
US08084484B2

Reaction notes

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