Sodium Hydroxide → 1-(1-Benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylic acid

HRID 1458000Notes

Reaction equation

HRID 1458000 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[CH2:14][CH:13]([C:15]2([C:18]([O:20]CC)=[O:19])[CH2:17][CH2:16]2)[CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+]>C(O)C>[CH2:1]([O:8][C:9]([N:11]1[CH2:12][CH:13]([C:15]2([C:18]([OH:20])=[O:19])[CH2:17][CH2:16]2)[CH2:14]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 54249419Ethyl 1-(1-benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylate

Product 1

HCID 542820731-(1-Benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylic acidYield 97%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 2.68 g (8.83 mmol) of ethyl 1-(1-benzyloxycarbonyl-3-azetidinyl)cyclopropanecarboxylate dissolved in 27 ml of ethanol was added 27 ml of 1N sodium hydroxide aqueous 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 (50 ml×3) and then dried over anhydrous sodium sulfate. By evaporating the solvent, 2.35 g (97%) 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 (50 ml×3)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customBy evaporating the solvent

Sources & evidence

ORD record
ord-3b9e912f4f134c10a7cfa9425467bc23
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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