Methyl iodide → HCID 57763199, compound

HRID 2101681Notes

Reaction equation

HRID 2101681 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH:10][C:11]3[C:20]4[C:15](=[C:16]([CH3:27])[CH:17]=[C:18]([S:21]([CH2:24][CH2:25][OH:26])(=[O:23])=[O:22])[CH:19]=4)[N:14]=[CH:13][C:12]=3[C:28]([NH2:30])=[O:29])[C:4]=2[CH2:3][CH2:2]1.[H-].[Na+].[CH3:33]I>CN(C)C=O>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([NH:10][C:11]3[C:20]4[C:15](=[C:16]([CH3:27])[CH:17]=[C:18]([S:21]([CH2:24][CH2:25][O:26][CH3:33])(=[O:22])=[O:23])[CH:19]=4)[N:14]=[CH:13][C:12]=3[C:28]([NH2:30])=[O:29])[C:4]=2[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 57763272HCID 57763272, compound

Product 1

HCID 57763199HCID 57763199, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of Example 523 (0.018 g) in dry N,N-dimethylformamide (1 ml) under nitrogen was added sodium hydride (60% dispersion in mineral oil, 0.0017 g). The mixture was stirred at room temperature for 10 min when methyl iodide (0.0026 ml) was added, stirring was continued for 18 h at room temperature and the solvent evaporated in vacuo. The residue was partitioned between ethyl acetate and water and the organic layer dried (MgSO4) and evaporated. The crude product was purified using mass directed preparative HPLC (Method A) to give the title compound as a yellow solid (0.0024 g).

Workup

  1. additionwas added
  2. customthe solvent evaporated in vacuo
  3. customThe residue was partitioned between ethyl acetate and water
  4. dry with materialthe organic layer dried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified

Sources & evidence

ORD record
ord-7d4e7444a0c24ee0bdb2547cda732faa
Source dataset
uspto-grants-2009_08
Patent number
US07572915B2

Reaction notes

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