Methyl iodide → HCID 10483456, compound

HRID 1613516Notes

Reaction equation

HRID 1613516 reaction equation
[S:1]=[C:2]1[NH:6][C:5]([C:7]2[CH:34]=[CH:33][C:10]([O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]3[CH:29]=[CH:28][C:19]4[CH2:20][CH2:21][CH:22]([C:24]([O:26][CH3:27])=[O:25])[O:23][C:18]=4[C:17]=3[CH2:30][CH2:31][CH3:32])=[C:9]([CH2:35][CH2:36][CH3:37])[C:8]=2[O:38][CH3:39])=[CH:4][S:3]1.[N+]([CH3:43])([O-])=O.CI>C(OCC)C.O>[CH3:39][O:38][C:8]1[C:9]([CH2:35][CH2:36][CH3:37])=[C:10]([CH:33]=[CH:34][C:7]=1[C:5]1[N:6]=[C:2]([S:1][CH3:43])[S:3][CH:4]=1)[O:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:29]=[CH:28][C:19]2[CH2:20][CH2:21][CH:22]([C:24]([O:26][CH3:27])=[O:25])[O:23][C:18]=2[C:17]=1[CH2:30][CH2:31][CH3:32]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 6375NitromethaneHCID 10483150HCID 10483150, compound

Product 1

HCID 10483456HCID 10483456, compoundYield 97.6%

Reagents, catalysts & solvents 1

HCID 21584184Diethylether waterSolvent

Procedure

The compound of Example 25 (18 mg, 31.4 μmol) was added to 1.0 ml of nitromethane, and 0.3 ml of methyl iodide was added. The mixture was allowed to react at room temperature for 1 hour. The reaction mixture was poured into ethyl ether/water, and the ether layer was washed with brine, dried over sodium sulfate, and concentrated. The crude product was chromatographed on silica gel using 20:1 to 10:1 hexane/ethyl acetate as eluant to give the product (51 mg, 87.0 μmol, 97.6% yield). High resolution mass spectrum, m/e 585.2223 (calculated for C31H39N6S2, 585.2219).

Workup

  1. additionwas added
  2. customto react at room temperature for 1 hour
  3. washthe ether layer was washed with brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product was chromatographed on silica gel using 20:1 to 10:1 hexane/ethyl acetate as eluant

Sources & evidence

ORD record
ord-31de5083c84147eab779dea9dcc7feb2
Source dataset
uspto-grants-1993_03
Patent number
US05192782

Reaction notes

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