Methyl iodide → HCID 69862800, compound

HRID 987923Notes

Reaction equation

HRID 987923 reaction equation
[H-].[Na+].[C:3]([O:7][C:8]([N:10]1[CH:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([CH2:22][CH:23]2[CH2:28][CH:27]([OH:29])[CH2:26][CH2:25][CH:24]2[C:30](=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[O:12][C:11]1([CH3:38])[CH3:37])=[O:9])([CH3:6])([CH3:5])[CH3:4].[CH3:39]I>CN(C)C=O>[C:3]([O:7][C:8]([N:10]1[CH:14]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:13]([CH2:22][CH:23]2[CH2:28][CH:27]([O:29][CH3:39])[CH2:26][CH2:25][CH:24]2[C:30](=[O:36])[NH:31][C:32]([CH3:35])([CH3:34])[CH3:33])[O:12][C:11]1([CH3:38])[CH3:37])=[O:9])([CH3:5])([CH3:6])[CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 698535414-Benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester

Product 1

HCID 69862800HCID 69862800, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (60% w/w in mineral oil, 20 mg, 0.52 mmol) was added to a solution of 4-benzyl-5-(2-tert-butylcarbamoyl-5-hydroxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (200 mg, 0.40 mmol) in dry N,N-dimethylformamid (4 ml) stirred at 0° C. under nitrogen. The resulting mixture was stirred at 0° C. until gas evolution had ceased. Methyl iodide (40 μl, 0.6 mmol) was then added, and the solution was allowed to warm to room temperature and stirred for 20 hours. After removal of the volatiles in vacuo, the crude product was dissolved in ethyl acetate, washed twice with water, dried (anhydrous magnesium sulfate) and concentrated in vacuo. Purification by flash chromatography on silica gel provided 4-benzyl-5-(2-tert-butylcarbamoyl-5-methoxy-cyclohexylmethyl)-2,2-dimethyl-oxazolidine-3-carboxylic acid tert-butyl ester (125 mg, 96%).

Workup

  1. stirringThe resulting mixture was stirred at 0° C. until gas evolution
  2. temperatureto warm to room temperature
  3. stirringstirred for 20 hours
  4. customAfter removal of the volatiles in vacuo
  5. dissolutionthe crude product was dissolved in ethyl acetate
  6. washwashed twice with water
  7. dry with materialdried (anhydrous magnesium sulfate)
  8. concentrationconcentrated in vacuo
  9. customPurification by flash chromatography on silica gel

Sources & evidence

ORD record
ord-7598962c875c468fb1eb964120f13bf6
Source dataset
uspto-grants-2003_10
Patent number
US06632826B1

Reaction notes

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