N-bromobutanimide → HCID 22494074, compound

HRID 1296207Notes

Reaction equation

HRID 1296207 reaction equation
[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:23][CH:24]([CH3:26])[CH3:25])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH:8]=1)[CH3:2].[Br:28]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:3][C:4](=[O:27])[CH:5]([O:23][CH:24]([CH3:26])[CH3:25])[CH2:6][C:7]1[CH:8]=[C:9]([CH2:14][NH:15][C:16]([O:18][C:19]([CH3:20])([CH3:21])[CH3:22])=[O:17])[C:10]([OH:13])=[C:11]([Br:28])[CH:12]=1)[CH3:2]

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 3-(3-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester was dissolved in 5 ml of acetonitrile, and 200 mg of N-bromosuccinimide was added thereto, followed by stirring for 1 hour at room temperature. The reaction mixture was diluted with ethyl acetate, and the organic layer was washed with water and brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography, to give 433 mg of 3-(3-bromo-5-[(t-butoxycarbonyl)amino]methyl-4-hydroxyphenyl)-2-isopropoxypropionic acid ethyl ester from fractions eluted with hexane-ethyl acetate (5:1).

Workup

  1. washthe organic layer was washed with water and brine
  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-5f8c8c26528a4834aabc5a384f7ce815
Source dataset
uspto-grants-2007_07
Patent number
US07244861B2

Reaction notes

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