Ethyl bromoacetate → HCID 22902037, compound

HRID 1489555Notes

Reaction equation

HRID 1489555 reaction equation
[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:14][C:7]=2[NH:6][C:5]1=[O:21])=[N+:2]=[N-:3].C(=O)([O-])[O-].[K+].[K+].O1CCCC1.Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36]>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[N:1]([CH:4]1[CH2:10][CH2:9][C:8]2[CH:11]=[CH:12][C:13]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:14][C:7]=2[N:6]([CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:5]1=[O:21])=[N+:2]=[N-:3]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8028TetrahydrofuranHCID 11430Potassium CarbonateHCID 22902051HCID 22902051, compound

Product 1

HCID 22902037HCID 22902037, compoundYield 81.3%

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8857Ethyl AcetateSolvent

Procedure

While stirring 30 ml of a mixture of 0.75 g (2.70 mmol) of 3-azido-8-phenyl-2,3,4,5-tetrahydro-1H-[1]benzazepin-2-one obtained in the Synthesis Example A-6, 0.093 g (0.288 mmol) of tetran- butylammonium bromide, 0.17 g (3.03 mmol) of powdery potassium carbonate and tetrahydrofuran at room temperature, 0.35 ml (3.16 mmol) of ethyl bromoacetate was added thereto, followed by stirring for 2 hours. After adding ethyl acetate to the reaction mixture, the obtained mixture was washed with water and a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate. After distilling off the solvent under reduced pressure, the residue was subjected to silica gel column chromatography. After eluting with hexane:ethyl acetate in a ratio of 15:1 (v/v), 0.8 g of the title compound was obtained as a pale yellow, oily product. Yield 81%.

Workup

  1. washthe obtained mixture was washed with water
  2. dry with materiala saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate
  3. distillationAfter distilling off the solvent under reduced pressure
  4. washAfter eluting with hexane

Sources & evidence

ORD record
ord-d8d9b17194084cff8f8e0db3239824d3
Source dataset
uspto-grants-1997_10
Patent number
US05679671

Reaction notes

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