Methyl iodide → HCID 11247989, compound

HRID 970146Notes

Reaction equation

HRID 970146 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@@:11]([CH:14]([O:17][CH3:18])[O:15][CH3:16])([CH3:13])[C@H:10]([OH:19])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[NH:22][C:21]3=[N:29][C:30]#[N:31])[C:8]=2[CH:32]=1)([O-:3])=[O:2].[C:33]([O-])([O-])=O.[K+].[K+].CI.C([O-])(O)=O.[Na+]>CN(C=O)C>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]2[O:12][C@@:11]([CH:14]([O:17][CH3:18])[O:15][CH3:16])([CH3:13])[C@H:10]([OH:19])[C@@H:9]([N:20]3[C:24]4[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=4[N:22]([CH3:33])[C:21]3=[N:29][C:30]#[N:31])[C:8]=2[CH:32]=1)([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 178499579HCID 178499579, compound

Product 1

HCID 11247989HCID 11247989, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

400 mg (0.91 mmol) of the compound obtained in example 1 was dissolved in 5 ml of DMF, then 250 mg (1.82 mmol) of K2CO3 and 170 mg (1.18 mmol) of CH3I were added thereto. The reaction was stirred at room temperature for 12 hours, 30 ml of saturated NaHCO3 solution was added, and aqueous layer was extracted with 50 ml of ethyl acetate. Organic layer was washed with brine and dried over anhydrous MgSO4, concentrated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1), to give 390 mg (yield: 95%) of the target compound.

Workup

  1. extractionaqueous layer was extracted with 50 ml of ethyl acetate
  2. washOrganic layer was washed with brine
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Sources & evidence

ORD record
ord-20a1f513a1ab46a39a59a0d4b654b18f
Source dataset
uspto-grants-2007_12
Patent number
US07309793B2

Reaction notes

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