Methyl iodide → HCID 58545029, compound

HRID 404155Notes

Reaction equation

HRID 404155 reaction equation
[C:1]([O-])([O-])=O.[K+].[K+].[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[CH:28][C:27]([OH:30])=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8].CI.CCOC(C)=O>CN(C=O)C.[Cl-].[Na+].O>[CH2:7]([O:9][C:10](=[O:31])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][N:17]([C:24]1[CH:29]=[CH:28][C:27]([O:30][CH3:1])=[CH:26][N:25]=1)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[CH3:8]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 58545020HCID 58545020, compound

Product 1

HCID 58545029HCID 58545029, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
50 °C

Procedure

K2CO3 (12 mg, 0.087 mmol) was added to compound II (20 mg, 0.058 mmol) in DMF (2 mL) at rt under Ar(g). After 15 min CH3I (0.004 mL, 0.058 mmol) was added and the reaction was stirred at 50° C. for 3 h30. Brine (15 mL) and EtOAc (15 mL) were added, then the phases were separated, and the aqueous phase was extracted with EtOAc (2×5 mL). The organic phases were combined then dried over MgSO4, filtered, and subsequently evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography eluting with hexane/EtOAc (80:20 then 70:30) to furnish III as a colourless oil (11.65 mg, 56%).

Workup

  1. customthe phases were separated
  2. extractionthe aqueous phase was extracted with EtOAc (2×5 mL)
  3. dry with materialThe organic phases were combined then dried over MgSO4
  4. filtrationfiltered
  5. customsubsequently evaporated under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography
  7. washeluting with hexane/EtOAc (80:20

Sources & evidence

ORD record
ord-582e83fb81e2457483835f3e74e9ce9c
Source dataset
uspto-grants-2014_06
Patent number
US08748458B2

Reaction notes

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