Methyl iodide → HCID 67909678, compound

HRID 1681224Notes

Reaction equation

HRID 1681224 reaction equation
[C:1]([CH:8]([O:23][NH2:24])[CH:9]([F:22])[CH2:10][NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])([O:3][C:4]([CH3:7])([CH3:6])[CH3:5])=[O:2].[OH-].[Na+].[CH3:27]I>C(O)C>[C:1]([CH:8]([O:23][NH2:24])[CH:9]([F:22])[CH2:10][N:11]([CH3:27])[S:12]([C:15]1[CH:16]=[CH:17][C:18]([CH3:21])=[CH:19][CH:20]=1)(=[O:13])=[O:14])([O:3][C:4]([CH3:6])([CH3:7])[CH3:5])=[O:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 57157470HCID 57157470, compound

Product 1

HCID 67909678HCID 67909678, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

0.54 g (1.5 mmol) of N-(3-BOC-aminoxy-2-fluoropropyl)-4-toluenesulfonamide are dissolved in 10 ml of ethanol and 1.5 ml of 1N sodium hydroxide solution and, after the addition of 0.21 g (1.5 mmol) of methyl iodide, maintained at 70° for 10 hours in a bomb tube. After cooling, the reaction mixture is concentrated by evaporation and the residue is taken up in ethyl acetate. The resulting solution is washed with water and dried over magnesium sulfate, yielding, after evaporation of the solvent, starting compound c.

Workup

  1. temperaturemaintained at 70° for 10 hours in a bomb tube
  2. temperatureAfter cooling
  3. concentrationthe reaction mixture is concentrated by evaporation
  4. washThe resulting solution is washed with water
  5. dry with materialdried over magnesium sulfate
  6. customyielding
  7. customafter evaporation of the solvent

Sources & evidence

ORD record
ord-c9eff2626e914ed98b6fbe148606000b
Source dataset
uspto-grants-1992_12
Patent number
US05169867

Reaction notes

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