Methyl iodide → 1-[[(3-Methyl-2-oxo-1-imidazolidinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

HRID 448737Notes

Reaction equation

HRID 448737 reaction equation
CI.[C:3]1([CH2:9][O:10][C:11]([C:13]2([NH:19][C:20]([N:22]3[CH2:26][CH2:25][NH:24][C:23]3=[O:27])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:28](=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:3]1([CH2:9][O:10][C:11]([C:13]2([NH:19][C:20]([N:22]3[CH2:26][CH2:25][N:24]([CH3:28])[C:23]3=[O:27])=[O:21])[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]2)=[O:12])[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 576728221-[[(2-Oxo-1-imidazolidinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester

Product 1

HCID 576728101-[[(3-Methyl-2-oxo-1-imidazolidinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl esterYield 50%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.83 g (12.9 mmol) of methyl iodide was added to a solution of 1.50 g (4.3 mmol) of 1-[[(2-oxo-1-imidazolidinyl)carbonyl]amino]cyclohexanecarboxylic acid phenylmethyl ester and 1.78 g (12.9 mmol) of potassium carbonate in 100 ml of acetonitrile, and the mixture was heated under reflux overnight. The reaction solution was concentrated, ethyl acetate was added thereto, and the mixture was successively washed with water, a 10% aqueous potassium hydrogensulfate solution, a saturated aqueous sodium hydrogencarbonate solution and saturated brine, followed by drying with anhydrous sodium sulfate. After the solvent was distilled off under reduced pressure, the residue was purified by silica gel chromatography to obtain 710 mg (50%) of the title compound.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux overnight
  3. concentrationThe reaction solution was concentrated
  4. additionethyl acetate was added
  5. washthe mixture was successively washed with water
  6. dry with materialby drying with anhydrous sodium sulfate
  7. distillationAfter the solvent was distilled off under reduced pressure
  8. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-18e115170978461a97a76152ad6e73c2
Source dataset
uspto-grants-2013_07
Patent number
US08481725B2

Reaction notes

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