Water → HCID 86612365, compound

HRID 2376288Notes

Reaction equation

HRID 2376288 reaction equation
[C:1]([O:5][C:6](=[O:22])[NH:7][C:8]1[C:9]([CH3:21])=[CH:10][C:11]2[O:15][C:14]([CH3:17])([CH3:16])[C:13](=[O:18])[C:12]=2[C:19]=1[CH3:20])([CH3:4])([CH3:3])[CH3:2].[Br:23]N1C(=O)CCC1=O.O>C(#N)C>[Br:23][C:10]1[C:11]2[O:15][C:14]([CH3:16])([CH3:17])[C:13](=[O:18])[C:12]=2[C:19]([CH3:20])=[C:8]([NH:7][C:6](=[O:22])[O:5][C:1]([CH3:4])([CH3:2])[CH3:3])[C:9]=1[CH3:21]

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 23113917HCID 23113917, compound

Product 1

HCID 86612365HCID 86612365, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of tert-butyl(2,2,4,6-tetramethyl-3-oxo-2,3-dihydro-1-benzofuran-5-yl)carbamate obtained in Reference Example 60 (4.86 g, 15.9 mmol) in acetonitrile (70 mL) was added N-bromosuccinimide (5.67 g, 31.8 mmol) was heated under reflux for 1.5 hours. The reaction solution was cooled to room temperature, followed by addition of water, which was extracted with ethyl acetate, and the organic layer was washed with water and a saturation brine, dried over anhydrous sodium sulfate, and then was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7), and then was recrystallized with ethyl acetate-hexane to obtain 4.40 g (yield 72%) of the title compound. Melting point: 131-132° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hours
  3. extractionwas extracted with ethyl acetate
  4. washthe organic layer was washed with water
  5. dry with materiala saturation brine, dried over anhydrous sodium sulfate
  6. concentrationwas concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:hexane=3:7)
  8. customwas recrystallized with ethyl acetate-hexane

Sources & evidence

ORD record
ord-894bf7b08f2842d6aaf3c245f74b6ae2
Source dataset
uspto-grants-2008_12
Patent number
US07465815B2

Reaction notes

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