Methyl iodide → HCID 67076719, compound

HRID 2405258Notes

Reaction equation

HRID 2405258 reaction equation
[CH3:1][O:2][C:3](=[O:20])[CH:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=1)[C:5]([O:7][CH3:8])=[O:6].[CH3:21]C(C)([O-])C.[K+].IC>CN(C=O)C>[CH3:8][O:7][C:5](=[O:6])[C:4]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH2:15][C:16]([O:18][CH3:19])=[O:17])[CH:10]=1)([CH3:21])[C:3]([O:2][CH3:1])=[O:20]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 23665647Potassium tert-butoxideHCID 67239285HCID 67239285, compound

Product 1

HCID 67076719HCID 67076719, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of step 1 (0.353 g, 1.26 mmol) was dissolved in DMF (1.5 ml), potassium tert-butoxide (151 mg, 1.32 mmol) was added, the mixture stirred at room temperature for 10 min, and then iodomethane (0.542 g, 3.78 mmol) was added. The mixture was stirred at room temperature for 3 h and partitioned between EA and 2 N hydrochloric acid. The combined extracts were washed with a saturated aqueous sodium chloride solution, dried over sodium sulfate and evaporated to dryness. The residue was purified by preparative RP HPLC (water/ACN gradient) to yield 0.128 g of the title compound.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 h
  2. custompartitioned between EA and 2 N hydrochloric acid
  3. washThe combined extracts were washed with a saturated aqueous sodium chloride solution
  4. dry with materialdried over sodium sulfate
  5. customevaporated to dryness
  6. customThe residue was purified by preparative RP HPLC (water/ACN gradient)

Sources & evidence

ORD record
ord-9f31ca03c10248b893581d41794af8a8
Source dataset
uspto-grants-2014_08
Patent number
US08802720B2

Reaction notes

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