Methyl iodide → HCID 90906720, compound

HRID 2183860Notes

Reaction equation

HRID 2183860 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22]#[N:23])=[C:6]([CH:21]=1)[O:7][C@@H:8]([CH2:19][OH:20])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15].I[CH3:25]>C(#N)C.[Ag]=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22]#[N:23])=[C:6]([CH:21]=1)[O:7][C@@H:8]([CH2:19][O:20][CH3:25])[CH2:9][CH2:10][NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:15])[CH3:16]

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 90956681HCID 90956681, compound

Product 1

HCID 90906720HCID 90906720, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 6342AcetonitrileSolvent

Procedure

The product from step (d) (380 mg, 1.12 mmol) was dissolved in acetonitrile (40 ml) and silver oxide (1.292 g, 5.58 mmol) and iodomethane (1.589 g, 11.2 mmol) added. The reaction was stirred at room temperature for 20 h, then at 60° C. for 3 days. The reaction was cooled and filtered. The filtrate was evaporated in vacuo and the residue chromatographed on flash silica, eluting with hexane:ethyl acetate (3:1, then 2:1), to afford the title compound as a colourless oil (146 mg, 37%).

Workup

  1. waitat 60° C. for 3 days
  2. temperatureThe reaction was cooled
  3. filtrationfiltered
  4. customThe filtrate was evaporated in vacuo
  5. customthe residue chromatographed on flash silica
  6. washeluting with hexane:ethyl acetate (3:1

Sources & evidence

ORD record
ord-feca1b91b9754ce690a2984436670888
Source dataset
uspto-grants-2005_05
Patent number
US06900243B2

Reaction notes

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