Methyl iodide → HCID 67246011, compound

HRID 2357040Notes

Reaction equation

HRID 2357040 reaction equation
[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:23])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])=[C:9]([OH:24])[CH:8]=1)[CH3:2].[C:26]([O-])([O-])=O.[K+].[K+].CI.[F-].[K+]>CN(C=O)C.O>[CH2:1]([O:3][C:4](=[O:25])[CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[O:23])[CH2:14][NH:15][C:16]([O:18][C:19]([CH3:21])([CH3:20])[CH3:22])=[O:17])=[C:9]([O:24][CH3:26])[CH:8]=1)[CH3:2]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 522689Potassium FluorideHCID 67247207HCID 67247207, compound

Product 1

HCID 67246011HCID 67246011, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a vigorously stirred solution of the compound of example 41e (4.5 g; 12.7 mmol) in dry DMF (20 ml) was added sequentially fused K2CO3 (3.5 g; 25.5 mmol), methyl iodide (0.96 ml; 15.3 mmol) and KF (0.45 g). The reaction mixture was stirred for 3 h, diluted with water (200 ml) and the oily residue was extracted with chloroform (3×30 ml). The organic layer was washed with brine, dried (Na2SO4), concentrated and purified using flash chromatography (silica gel, 3% CH3CN in chloroform). Yield, 3.25 g (69.5%); mp, 75° C.; MS (ESI+): 390 (M++Na), 368 (M++1); analysis: C18H25NO7 requires C, 58.85; H, 6.85; N, 3.81; found: C, 58.79; H, 7.26; N, 3.81%.

Workup

  1. extractionthe oily residue was extracted with chloroform (3×30 ml)
  2. washThe organic layer was washed with brine
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified
  6. customYield
  7. custommp, 75° C.

Sources & evidence

ORD record
ord-570fce372ccf4c6aadd9b892bc469faa
Source dataset
uspto-grants-2010_07
Patent number
US07759387B2

Reaction notes

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