Water → 1-(((Tert-butoxy)carbonyl)(methyl)amino)cyclopropane-1-carboxylic acid

HRID 34095Notes

Reaction equation

HRID 34095 reaction equation
C([O:3][C:4]([C:6]1([N:9]([C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[CH3:10])[CH2:8][CH2:7]1)=[O:5])C.O>CO.[OH-].[Na+]>[C:14]([O:13][C:11]([N:9]([CH3:10])[C:6]1([C:4]([OH:5])=[O:3])[CH2:8][CH2:7]1)=[O:12])([CH3:17])([CH3:16])[CH3:15]

Participants

5

Reactant 2

HCID 962WaterHCID 60035001HCID 60035001, compound

Product 1

HCID 143582621-(((Tert-butoxy)carbonyl)(methyl)amino)cyclopropane-1-carboxylic acidYield 84.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 48 mg of 1-(tert-butoxycarbonyl-methyl-amino)-cyclopropane carboxylic acid ethyl ester in 0.4 mL of methanol, 0.1 mL of 5N sodium hydroxide aqueous solution was added and stirred at room temperature overnight. After adding water, the reaction solution was washed with diethyl ether. The aqueous layer was added with 0.7 mL of 1N hydrochloric acid, and extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated, to afford 36 mg of the title compound as white crystals.

Workup

  1. washthe reaction solution was washed with diethyl ether
  2. additionThe aqueous layer was added with 0.7 mL of 1N hydrochloric acid
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated

Sources & evidence

ORD record
ord-43da8811c64045d3a48752a2122937b7
Source dataset
uspto-grants-2008_09
Patent number
US07429609B2

Reaction notes

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