Potassium hydroxide ethanol → Ethyl hydrogen (1-benzyloxycarbonyl-3-azetidinyl)malonate

HRID 1457997Notes

Reaction equation

HRID 1457997 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH:15]([C:21]([O:23]CC)=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(O)C.[OH-].[K+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([CH:15]([C:21]([OH:23])=[O:22])[C:16]([O:18][CH2:19][CH3:20])=[O:17])[CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 21946426Potassium hydroxide ethanolHCID 54152329Diethyl (1-benzyloxycarbonyl-3-azetidinyl)malonate

Product 1

HCID 53765389Ethyl hydrogen (1-benzyloxycarbonyl-3-azetidinyl)malonate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 13.43 g (38.33 mmol) of diethyl (1-benzyloxycarbonyl-3-azetidinyl)malonate dissolved in 130 ml of ethanol was added 38.44 ml of 1N potassium hydroxide ethanol solution, followed by overnight stirring at room temperature. After evaporation of the solvent, the resulting residue was mixed with 10% citric acid aqueous solution, extracted with chloroform (200 ml×3) and then dried over anhydrous sodium sulfate. By evaporating the solvent, quantitative amount of the title compound was obtained.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe resulting residue was mixed with 10% citric acid aqueous solution
  3. extractionextracted with chloroform (200 ml×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customBy evaporating the solvent, quantitative amount of the title compound
  6. customwas obtained

Sources & evidence

ORD record
ord-ab1491196a9c433e8b2f716691c23701
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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