Methyl iodide → HCID 22494028, compound

HRID 1816600Notes

Reaction equation

HRID 1816600 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH2:18][CH:19]([O:25][CH:26]([CH3:28])[CH3:27])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([CH2:9][NH:10][C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])[C:7]=1[OH:8].IC.[C:31](=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([CH2:18][CH:19]([O:25][CH:26]([CH3:27])[CH3:28])[C:20]([O:22][CH2:23][CH3:24])=[O:21])[CH:5]=[C:6]([CH2:9][NH:10][C:11]([O:13][C:14]([CH3:16])([CH3:17])[CH3:15])=[O:12])[C:7]=1[O:8][CH3:31]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22494074HCID 22494074, compound

Product 1

HCID 22494028HCID 22494028, compoundYield 90.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

944 mg of ethyl 3-(3-bromo-5-[(tertiary butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionate was dissolved in 5 ml N,N-dimethylformamide, and 0.15 ml iodomethane and 500 mg of potassium carbonate were successively added. After stirring at room temperature for 2 hours, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous magnesium sulfate and the solvent was evapoarated. The residue was purified by silica gel column chromatography, and from fractions eluted with hexane-ethyl acetate (4:1), 876 mg of ethyl 3-(3-bromo-5-[(tertiary butoxycarbonyl)amino]methyl-4-methoxyphenyl)-2-isopropoxypropionate was obtained.

Workup

  1. washThe organic layer was washed with water and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customThe residue was purified by silica gel column chromatography
  4. washfrom fractions eluted with hexane-ethyl acetate (4:1)

Sources & evidence

ORD record
ord-b9ef82dc57524c828a62de6e651c76a4
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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