Methyl iodide → HCID 59128635, compound

HRID 1991018Notes

Reaction equation

HRID 1991018 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[CH2:7]([C:11]1[O:15][C:14]([C:16]2[CH:17]=[CH:18][C:19]([CH3:26])=[C:20]([CH2:22][C:23]([OH:25])=[O:24])[CH:21]=2)=[N:13][N:12]=1)[CH:8]([CH3:10])[CH3:9].IC>CN(C)C=O>[CH3:1][O:24][C:23](=[O:25])[CH2:22][C:20]1[CH:21]=[C:16]([C:14]2[O:15][C:11]([CH2:7][CH:8]([CH3:10])[CH3:9])=[N:12][N:13]=2)[CH:17]=[CH:18][C:19]=1[CH3:26]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 59128630HCID 59128630, compound

Product 1

HCID 59128635HCID 59128635, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of potassium carbonate (0.56 g, 4.05 mmol), [5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl]-acetic acid (1.01 g, 3.68 mmol) and iodomethane (0.33 mL, 5.26 mmol) in N,N-dimethylformamide (10 mL) was stirred at room temperature for 2 days. The reaction mixture was partitioned between ethyl acetate and water. The combined organic phase was washed with water and brine, dried (magnesium sulfate), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography eluting with 0-40% ethyl acetate in hexanes to give [5-(5-isobutyl-[1,3,4]oxadiazol-2-yl)-2-methyl-phenyl]-acetic acid methyl ester (Yield: 0.54 g, 51%).

Workup

  1. customThe reaction mixture was partitioned between ethyl acetate and water
  2. washThe combined organic phase was washed with water and brine
  3. dry with materialdried (magnesium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash chromatography
  7. washeluting with 0-40% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-34b1df8311e1448db4aa21dad81b12e6
Source dataset
uspto-grants-2010_01
Patent number
US07645764B2

Reaction notes

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