Methyl iodide → HCID 70113590, compound

HRID 324435Notes

Reaction equation

HRID 324435 reaction equation
[H-].[Na+].[OH:3][C:4]1([C:20]2[C:21](=[O:27])[NH:22][C:23](=[O:26])[NH:24][CH:25]=2)[C:13]2[S:12][C:11]([CH3:14])=[N:10][C:9]=2[CH2:8][CH2:7][C:6]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:5]1=2.[CH3:28]I>CN(C)C=O>[CH3:28][N:24]1[CH:25]=[C:20]([C:4]2([OH:3])[C:13]3[S:12][C:11]([CH3:14])=[N:10][C:9]=3[CH2:8][CH2:7][C:6]3[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:5]2=3)[C:21](=[O:27])[NH:22][C:23]1=[O:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70114562HCID 70114562, compound

Product 1

HCID 70113590HCID 70113590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60% dispersion by wt) (112 mg) was added to a stirred solution of the product from step (v) (1.0 g) in N,N-dimethylformamide (20 ml) at room temperature. After 0.75 h, methyl iodide (0.175 ml) was added and stirring continued for 1 h. The mixture was quenched with water and extracted with ethyl acetate. The organic phase was washed with water, dried (MgSO4) and evaporated under reduced pressure. Purification was by chromatography eluting with 5% methanol in dichloromethane.

Workup

  1. waitcontinued for 1 h
  2. customThe mixture was quenched with water
  3. extractionextracted with ethyl acetate
  4. washThe organic phase was washed with water
  5. dry with materialdried (MgSO4)
  6. customevaporated under reduced pressure
  7. customPurification
  8. washeluting with 5% methanol in dichloromethane

Sources & evidence

ORD record
ord-4f38762c25fd481c81fc2f8fcccda0b0
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Reaction notes

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