Methyl iodide → HCID 67711340, compound

HRID 974860Notes

Reaction equation

HRID 974860 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([CH:8]1[NH:13][C:12](=[O:14])[CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:10]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[C:9]1=[O:26])=[O:7])[CH3:4].[CH3:27]I.[Cl-].[NH4+]>CN(C)C=O>[CH2:3]([O:5][C:6]([C:8]1([CH3:27])[NH:13][C:12](=[O:14])[CH:11]([CH2:15][CH:16]([CH3:18])[CH3:17])[N:10]([O:19][CH:20]2[CH2:25][CH2:24][CH2:23][CH2:22][O:21]2)[C:9]1=[O:26])=[O:7])[CH3:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 19969552HCID 19969552, compound

Product 1

HCID 67711340HCID 67711340, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.04 g of 60% sodium hydride was added to 100 ml of 9.67 g of 3-ethoxycarbonyl-6-isobutyl-1-(2-tetrahydropyranyloxy)piperazine-2,5-dione in anhydrous N,N-dimethylformamide, on ice cooling, and the mixture was stirred for 10 minutes. Thereto was added 3.5 ml of methyl iodide. The mixture was stirred at room temperature for 5 hours. The reaction mixture was ice-cooled and poured into an aqueous solution saturated with ammonium chloride. The mixture was extracted with ethyl acetate. The extract was washed three times with an aqueous solution saturated with sodium chloride, dried with anhydrous magnesium sulfate, and subjected to distillation to remove the solvent to obtain 8.53 g of (3RS,6SR)-3-ethoxycarbonyl-6-isobutyl-3-methyl-1-(2-tetrahydropyranyloxy)piperazine-2,5-dione as a brown oily substance.

Workup

  1. stirringThe mixture was stirred at room temperature for 5 hours
  2. temperaturecooled
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe extract was washed three times with an aqueous solution saturated with sodium chloride
  5. dry with materialdried with anhydrous magnesium sulfate
  6. distillationsubjected to distillation
  7. customto remove the solvent

Sources & evidence

ORD record
ord-129dbc3c4365457083ae4e7b63dc04b8
Source dataset
uspto-grants-1997_03
Patent number
US05607934

Reaction notes

Loading…