Sodium Hydroxide → Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-

HRID 1457985Notes

Reaction equation

HRID 1457985 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([O:15]CC)=[O:14])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+]>CO>[C:1]([O:5][C:6]([NH:8][C:9]1([C:13]([OH:15])=[O:14])[CH2:12][CH2:11][CH2:10]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10421885Cyclobutanecarboxylic acid, 1-[[(1,1-dimethylethoxy)carbonyl]amino]-, ethyl ester

Product 1

HCID 1512646Cyclobutanecarboxylic acid, 1-(((1,1-dimethylethoxy)carbonyl)amino)-Yield 97%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 64.28 g (264 mmol) portion of ethyl 1-tert-butoxycarbonylaminocyclobutanecarboxylate was dissolved in 400 ml of methanol, mixed with 400 ml of 1N sodium hydroxide aqueous solution and then stirred overnight at room temperature. After evaporation of the solvent, the resulting residue was mixed with 20% citric acid aqueous solution-chloroform. The resulting organic layer was dried over anhydrous sodium sulfate and the solvent was evaporated to yield 55.29 g (97%) of the title compound.

Workup

  1. customAfter evaporation of the solvent
  2. additionthe resulting residue was mixed with 20% citric acid aqueous solution-chloroform
  3. dry with materialThe resulting organic layer was dried over anhydrous sodium sulfate
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-e83f304da06841cca777dc90edd8bbd0
Source dataset
uspto-grants-1998_12
Patent number
US05849757

Reaction notes

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