Ethanol → HCID 17862027, compound

HRID 2109323Notes

Reaction equation

HRID 2109323 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 ref lux 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 under ref lux for 8 hours
  2. customthe solvent was removed under reduced pressure
  3. extractionThe residual aqueous solution was extracted with ethyl acetate
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-17e91db2a6fc4e60b3f50ed1202608c9
Source dataset
uspto-grants-2009_04
Patent number
US07514475B2

Reaction notes

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