Ethanol → HCID 17862027, compound

HRID 1785344Notes

Reaction equation

HRID 1785344 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:13][CH3:14])[CH2:9][C:10]([OH:12])=[O:11])[CH:5]=[CH:6][CH:7]=1.S(=O)(=O)(O)O.C(=O)([O-])O.[Na+].[CH2:25](O)[CH3:26]>>[OH:1][C:2]1[CH:3]=[C:4]([CH:8]([NH:13][CH3:14])[CH2:9][C:10]([O:12][CH2:25][CH3:26])=[O:11])[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 4

HCID 702EthanolHCID 1118Sulfuric AcidHCID 516892Sodium BicarbonateHCID 17862086HCID 17862086, compound

Product 1

HCID 17862027HCID 17862027, compound

Procedure

3-(3-Hydroxyphenyl)-3-methylaminopropionic acid (24.1 g) obtained from Example 7a was dissolved in ethanol (200 ml), and concentrated sulfuric acid (10 ml) was added dropwise to the solution. The resulting mixture was heated under reflux for 8 hours. The reaction mixture was neutralized with saturated aqueous sodium hydrogencarbonate solution and the solvent was removed under reduced pressure. The residual aqueous solution was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate and concentrated under reduced pressure to afford the desired compound which was used in next step reaction without further purification.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureunder reflux for 8 hours
  3. customthe solvent was removed under reduced pressure
  4. extractionThe residual aqueous solution was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-b897c681614b41c69f2c1fde9b55d1b8
Source dataset
uspto-grants-2009_03
Patent number
US07504437B2

Reaction notes

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