N-bromobutanimide → HCID 22494074, compound

HRID 1816599Notes

Reaction equation

HRID 1816599 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]1[CH:11]=[C:12]([CH2:17][CH:18]([O:24][CH:25]([CH3:27])[CH3:26])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:13]=[CH:14][C:15]=1[OH:16])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:35])C(=O)C1>C(#N)C.C(OCC)(=O)C>[Br:35][C:14]1[CH:13]=[C:12]([CH2:17][CH:18]([O:24][CH:25]([CH3:26])[CH3:27])[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH:11]=[C:10]([CH2:9][NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[C:15]=1[OH:16]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 22494161HCID 22494161, compound

Product 1

HCID 22494074HCID 22494074, compoundYield 89.3%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

402 mg of ethyl 3-(3-[(tertiary butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionate was dissolved in 5 ml acetonitrile, and 200 mg N-bromosuccimide was added. After stirring at room temperature for 1 hour, the reaction mixture was diluted with ethyl acetate. The organic layer was successively 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 (5:1), 433 mg of ethyl 3-(3-bromo-5-[(tertiary butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionate was obtained.

Workup

  1. washThe organic layer was successively 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 (5:1)

Sources & evidence

ORD record
ord-0ec408ff36284739899db925526e7498
Source dataset
uspto-grants-2005_04
Patent number
US06884821B1

Reaction notes

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