N-Iodosuccinimide → HCID 22494282, compound

HRID 1816609Notes

Reaction equation

HRID 1816609 reaction equation
Br[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].[I:29]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[I:29][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]

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

Workup

  1. washThe organic layer was washed with water and saturated aqueous sodium thiosulfate
  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-77a6e6f5f023418680cbbb4814a405d1
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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