Methyl iodide → HCID 59792950, compound

HRID 31555Notes

Reaction equation

HRID 31555 reaction equation
[OH:1][C@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12](/[CH:15]=[CH:16]/[CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[C:23](=[O:31])[C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[CH:11][CH:10]=1)[C:3]([OH:5])=[O:4].[H-].[Na+].[CH3:34]I.S([O-])(O)(=O)=O.[K+]>C1COCC1>[CH3:34][O:1][C@H:2]([CH2:6][O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12](/[CH:15]=[CH:16]/[CH2:17][N:18]2[CH:22]=[CH:21][CH:20]=[C:19]2[C:23](=[O:31])[C:24]2[CH:25]=[CH:26][C:27]([CH3:30])=[CH:28][CH:29]=2)=[CH:13][CH:14]=1)[C:3]([OH:5])=[O:4]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516920Potassium bisulfateHCID 59792858HCID 59792858, compound

Product 1

HCID 59792950HCID 59792950, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 69-2 (24 mg, 0.05 mmol) was dissolved in THF (1 ml), and thereto was added sodium hydride (5 mg, 0.11 mmol) under ice-cooling. The mixture was warmed to room temperature, and stirred for 30 minutes, and thereto was added methyl iodide (15 mg, 0.11 mmol). The mixture was stirred at room temperature for 2 hours, and thereto was added a 5% aqueous potassium hydrogen sulfate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated saline, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure to give the title compound.

Workup

  1. temperaturecooling
  2. stirringThe mixture was stirred at room temperature for 2 hours
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with saturated saline
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-9c9e82c92ca4405983546cd6640077cf
Source dataset
uspto-grants-2008_09
Patent number
US07425642B2

Reaction notes

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