Water → HCID 15170716, compound

HRID 486881Notes

Reaction equation

HRID 486881 reaction equation
[CH3:1][O:2][C:3]1[CH:31]=[CH:30][C:6]([CH2:7][S:8][CH2:9][C@@H:10]([C:27]([OH:29])=[O:28])[NH:11][C:12](=[O:26])[C:13]([S:16][CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH3:25])=[CH:20][CH:19]=2)([CH3:15])[CH3:14])=[CH:5][CH:4]=1.[H-].[Na+].[CH3:34]I.O>CN(C)C=O>[CH3:34][O:28][C:27](=[O:29])[C@H:10]([CH2:9][S:8][CH2:7][C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:31][CH:30]=1)[NH:11][C:12](=[O:26])[C:13]([S:16][CH2:17][C:18]1[CH:19]=[CH:20][C:21]([O:24][CH3:25])=[CH:22][CH:23]=1)([CH3:15])[CH3:14]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 15170715S-p-Methoxybenzyl-N-(2-p-Methoxybenzylthio-2-Methylpropionyl)-L-Cysteine

Product 1

HCID 15170716HCID 15170716, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of S-p-methoxybenzyl-N-(2-p-methoxybenzylthio-2-methylpropionyl)-L-cysteine (3.0 g) in dimethylformamide(20 ml), sodium hydride(0.3 g) was added under nitrogen atomosphere at room temperature and the mixture was stirred for 1 hour. Methyl iodide(0.5 ml) was added to the mixture. The reaction mixture was stirred for 4 hours at room temperature. Water(300 ml) was added to the reaction mixture and extracted with ether. The organic layer was washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by a silica gel column chromatography to give 2.8 g(90%) of the titled compound.

Workup

  1. stirringThe reaction mixture was stirred for 4 hours at room temperature
  2. extractionextracted with ether
  3. washThe organic layer was washed with saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe oily residue was purified by a silica gel column chromatography

Sources & evidence

ORD record
ord-12e8bc87d93e4bd0b284ee29067f142d
Source dataset
uspto-grants-1994_03
Patent number
US05292926

Reaction notes

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