Ethyl bromoacetate → HCID 58406051, compound

HRID 217976Notes

Reaction equation

HRID 217976 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6].[Cl-].[NH4+].[C:12]([O:15][CH2:16]C)(=[O:14])C.CN1[CH2:23][CH2:22][CH2:21][C:20]1=[O:24]>>[CH3:16][O:15][CH2:12][O:14][C@H:21]([CH:22]=[CH2:23])[CH2:20][O:24][CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

6

Reactant 5

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 13387N-methyl-2-pyrrolidoneHCID 24758Sodium hydrideHCID 25517Ammonium Chloride

Product 1

HCID 58406051HCID 58406051, compound

Procedure

Sodium hydride (2.5 g) was added to a solution of the compound obtained in Preparation Example 8-(3) (4.15 g) in 1-methyl-2-pyrrolidinone (60 mL) under ice-cooling. The reaction solution was stirred at the same temperature for 30 minutes. Ethyl bromoacetate (10.4 mL) was added dropwise to the reaction solution. The reaction solution was heated to room temperature and stirred at the same temperature for five hours. Saturated aqueous ammonium chloride and ethyl acetate were added to the reaction solution, and the organic layer was separated. The organic layer was washed with aqueous sodium chloride and then dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound (4.77 g).

Workup

  1. temperaturecooling
  2. stirringstirred at the same temperature for five hours
  3. customthe organic layer was separated
  4. washThe organic layer was washed with aqueous sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe organic layer was concentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-a8a079e6fba34c9489854b5e03505d25
Source dataset
uspto-grants-2012_06
Patent number
US08198269B2

Reaction notes

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