Ethyl bromoacetate → HCID 19689412, compound

HRID 583102Notes

Reaction equation

HRID 583102 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([OH:21])[CH:14]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+]>CC(=O)CC>[CH2:1]([O:8][C:9]([NH:11][CH2:12][C:13]1[CH:18]=[CH:17][C:16]([O:19][CH3:20])=[C:15]([O:21][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])[CH:14]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 11219914benzyl N-[(3-hydroxy-4-methoxyphenyl)methyl]carbamate

Product 1

HCID 19689412HCID 19689412, compoundYield 68.6%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A mixture comprising 20 g of N-benzyloxycarbonyl-3-hydroxy-4-methoxybenzylamine, 17.43 g of ethyl bromoacetate, 14.43 g of potassium carbonate and 200 ml of 2-butanone, was refluxed under heating with stirring overnight. The mixture was cooled to room temperature. Then, inorganic substances were filtered off, and the filtrate was distilled under reduced pressure. The obtained residue was extracted with chloroform, and the organic layer was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was crystallized from diethyl ether/n-hexane to obtain 17.83 g of the above-identified compound as white crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. filtrationThen, inorganic substances were filtered off
  4. distillationthe filtrate was distilled under reduced pressure
  5. extractionThe obtained residue was extracted with chloroform
  6. washthe organic layer was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customThe obtained residue was crystallized from diethyl ether/n-hexane

Sources & evidence

ORD record
ord-82286defef4b486fb96abf1739796345
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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