Water → HCID 13508648, compound

HRID 580033Notes

Reaction equation

HRID 580033 reaction equation
[CH2:1]([O:8][C:9]([O:11][NH:12][C:13](=[O:17])[CH2:14][CH:15]=[CH2:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].O.[Br:25]N1C(=O)CCC1=O>C(#N)C.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([O:11][N:12]1[CH:15]([CH2:16][Br:25])[CH2:14][C:13]1=[O:17])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 67184N-bromobutanimideHCID 13508644HCID 13508644, compound

Product 1

HCID 13508648HCID 13508648, compoundYield 116.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.3 g (1.28 mmole) of N-benzyloxycarbonyloxy but-3-eneoic acid amide in 20 ml of acetonitrile was added 0.1857 g (1.36 mmole) of potassium carbonate followed by 2 ml of water. The mixture was stirred vigorously for one minute and a solution of 0.2383 g (1.34 mmole) of N-bromosuccinimide in 5 ml of acetonitrile was added dropwise over 5 minutes with continued vigorous stirring. Stirring was continued for 10 minutes post addition and then the mixture was diluted with 200 ml of ethyl acetate. The solution was washed with water, aqueous 10% sodium bisulfite and brine and was dried over magnesium sulfate. The solvent was evaporated to provide 0.4686 g of the title compound as a pale yellow oil. The product was contaminated with minor amounts of succinimide and N-hydroxy-4-bromomethylazetidinone.

Workup

  1. stirringStirring
  2. additionwas continued for 10 minutes post addition
  3. washThe solution was washed with water, aqueous 10% sodium bisulfite and brine
  4. dry with materialwas dried over magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-41d3044099ee437e9f6245e4f3234d31
Source dataset
uspto-grants-1988_06
Patent number
US04751296

Reaction notes

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