Methyl iodide → HCID 22941055, compound

HRID 342132Notes

Reaction equation

HRID 342132 reaction equation
[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][OH:16])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH3:24])[C:10](=[O:25])[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:26]I.[H-].[Na+]>CN(C=O)C>[C:1]([O:5][C:6]([N:8]1[C@@H:13]([CH2:14][CH2:15][O:16][CH3:26])[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH3:23])[C:18]=2[CH3:24])[C:10](=[O:25])[CH2:9]1)=[O:7])([CH3:2])([CH3:4])[CH3:3]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 22941054HCID 22941054, compound

Product 1

HCID 22941055HCID 22941055, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product from Step E (0.241 g, 0.699 mmol) was dissolved in DMF (10 mL) containing methyl iodide (0.21 mL, 3.44 mmol) and the stirred solution cooled to 0° C. under nitrogen. Sodium hydride (0.070 g, 60% dispersion in oil, 1.72 mmol) was added and the reaction stirred for 1 h. The reaction was quenched with water, and the DMF removed under vacuum. The residue was partitioned between ethyl acetate and water, and the organic phase washed with saturated brine and dried over magnesium sulfate. The crude product was chromatographed on silica gel with 40% ethyl acetate in hexane to give the title compound.

Workup

  1. customThe reaction was quenched with water
  2. customthe DMF removed under vacuum
  3. customThe residue was partitioned between ethyl acetate and water
  4. washthe organic phase washed with saturated brine
  5. dry with materialdried over magnesium sulfate
  6. customThe crude product was chromatographed on silica gel with 40% ethyl acetate in hexane

Sources & evidence

ORD record
ord-258fff7357084286a519d781c14d2acd
Source dataset
uspto-grants-1999_01
Patent number
US05856326

Reaction notes

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