Methyl iodide → HCID 59861579, compound

HRID 1672091Notes

Reaction equation

HRID 1672091 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:21])[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][NH:13]2)=[CH:8][CH:7]=1.[C:22](=O)([O-])[O-].[K+].[K+].IC>CN(C=O)C>[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:15]=[C:14]2[C:9]([C:10](=[O:21])[C:11]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:12][N:13]2[CH3:22])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59861577HCID 59861577, compound

Product 1

HCID 59861579HCID 59861579, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 8 was dissolved in anhydrous DMF (Aldrich) in a 500 mL 1-neck round bottom flask. Anhydrous potassium carbonate (EM Science) was added and the mixture was stirred for 15 min. After addition of iodomethane (Aldrich), the mixture was stirred at room temperature overnight, after which it was concentrated and partitioned between CH2Cl2 and aq. sodium thiosulfate. The CH2Cl2 layer was rinsed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated to 19.30 g crude 9 (brownish solid). 1H NMR spectrum was satisfactory; however, TLC (MeOH:DCM 1:9) shows small amounts of lower polarity impurities and some high polarity impurities (possibly largely inorganic). Attempts to purify via re-precipitation from THF/water or CH2Cl2/hexane were unsatisfactory. Chromatography on a silica gel plug (gradient 1-2-4-6-10% methanol in CH2Cl2) provided purified product (17.93 g, 95% yield).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. concentrationafter which it was concentrated
  3. custompartitioned between CH2Cl2 and aq. sodium thiosulfate
  4. washThe CH2Cl2 layer was rinsed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated to 19.30 g crude 9 (brownish solid)
  8. customto purify via re-precipitation from THF/water or CH2Cl2/hexane
  9. customChromatography on a silica gel plug (gradient 1-2-4-6-10% methanol in CH2Cl2) provided

Sources & evidence

ORD record
ord-3512daac091d46baa810bf6dd1d17213
Source dataset
uspto-grants-2011_08
Patent number
US07998462B2

Reaction notes

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