Potassium Hydroxide → 3-[(Furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoic acid

HRID 1511602Notes

Reaction equation

HRID 1511602 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][CH2:9][C:10]([O:12]CC)=[O:11].[OH-].[K+]>CO>[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[CH2:6][N:7]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 243303Ethyl 3-[(furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoate

Product 1

HCID 684123413-[(Furan-2-ylmethyl)(ethoxycarbonyl)amino]propanoic acidYield 101.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ethyl 3-[(furan-2-ylmethyl) (ethoxycarbonyl)amino]-propionate (13.77 g) prepared in the step 3 was dissolved in 200 mL of methanol, 5.0 g of potassium hydroxide was added thereto and the mixture was heated to reflux for 3 hours. The solvent of the reaction solution was evaporated in vacuo and the residue was dissolved in methylene chloride. The resulting solution was slowly neutralized to pH 3 using 1N aqueous solution of hydrochloric acid (about 80 mL) with stirring. The organic layer was separated, washed with water and a saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate and the solvent was evaporated in vacuo therefrom to give 12.56 g of the objective compound as yellow liquid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. customThe solvent of the reaction solution was evaporated in vacuo
  4. dissolutionthe residue was dissolved in methylene chloride
  5. customThe organic layer was separated
  6. washwashed with water
  7. dry with materiala saturated solution of sodium chloride successively and dried over anhydrous magnesium sulfate
  8. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-b587a6a87e9248b1bc57ffc26c699811
Source dataset
uspto-grants-2012_07
Patent number
US08217031B2

Reaction notes

Loading…