Methyl iodide → HCID 59909806, compound

HRID 1279839Notes

Reaction equation

HRID 1279839 reaction equation
[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([NH:26][CH2:27][C:28]([O:30][CH3:31])=[O:29])=[O:25])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.IC.[C:34](=O)([O-])[O-].[Cs+].[Cs+]>CS(C)=O.O>[CH:1]1([CH2:7][CH2:8][CH2:9][C@@H:10]([C:19]2[O:23][N:22]=[C:21]([C:24]([N:26]([CH2:27][C:28]([O:30][CH3:31])=[O:29])[CH3:34])=[O:25])[N:20]=2)[CH2:11][C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 59909752HCID 59909752, compound

Product 1

HCID 59909806HCID 59909806, compoundYield 69.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

A solution of tert-butyl (3R)-6-cyclohexyl-3-(3-{[(2-methoxy-2-oxoethyl)amino]carbonyl}-1,2,4-oxadiazol-5-yl)hexanoate (Preparation 37) (440 mg, 1.00 mmol) in anhydrous dimethylsulphoxide (10 ml) was treated with iodomethane (310 μl, 5.00 mmol) and cesium carbonate (975 mg, 3.00 mmol) and the resulting mixture was heated at 40° under a nitrogen atmosphere for 3 hours then stirred at room temperature for 17 hours. The mixture was diluted with water and extracted with diethyl ether (×3). The combined organic extracts were washed with brine, dried over anhydrous sodium sulphate, filtered and the solvent removed under reduced pressure. The residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (2:1) to afford the title compound as a colourless oil (315 mg)

Workup

  1. temperaturethe resulting mixture was heated at 40° under a nitrogen atmosphere for 3 hours
  2. extractionextracted with diethyl ether (×3)
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel eluting with hexane:ethyl acetate (2:1)

Sources & evidence

ORD record
ord-367c4c5fe81a4a6c912bfd350e6c811d
Source dataset
uspto-grants-2002_09
Patent number
US06448278B2

Reaction notes

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