N-Iodosuccinimide → HCID 22494282, compound

HRID 1296213Notes

Reaction equation

HRID 1296213 reaction equation
[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:24][CH:25]([CH3:27])[CH3:26])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([OH:22])=[C:9](Br)[CH:8]=1)[CH3:2].[I:29]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:28])[CH:5]([O:24][CH:25]([CH3:27])[CH3:26])[CH2:6][C:7]1[CH:12]=[C:11]([CH2:13][NH:14][C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[C:10]([OH:22])=[C:9]([I:29])[CH:8]=1)[CH3:2]

Participants

5

Reactant 2

HCID 120273N-IodosuccinimideHCID 22494074HCID 22494074, compound

Product 1

HCID 22494282HCID 22494282, compoundYield 35.9%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

253 mg of 3-(3-bromo-5-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester was dissolved in 3 ml of acetonitrile, and 157 mg of N-iodosuccinimide was added. After stirring for 2.5 days at room temperature, the reaction mixture was diluted with ethyl acetate. The organic layer was washed with water and saturated sodium thiosulfate water, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, and 100 mg of 3-(3-iodo-5-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester was obtained from fractions eluted with hexane-ethyl acetate (4:1).

Workup

  1. washThe organic layer was washed with water and saturated sodium thiosulfate water
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-99bcbc1602a8436b9a7242421b27a5c7
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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