Ethyl bromoacetate → HCID 15550516, compound

HRID 1386629Notes

Reaction equation

HRID 1386629 reaction equation
[CH3:1][CH:2]([C:7]([C:9]1[C:10]([CH3:18])=[N:11][N:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=12)=[O:8])[C:3]([O:5][CH3:6])=[O:4].[H-].[Na+].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24].[Cl-].[NH4+]>O.CN(C=O)C>[CH3:18][C:10]1[C:9]([C:7](=[O:8])[C:2]([C:3]([O:5][CH3:6])=[O:4])([CH3:1])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 15550515HCID 15550515, compound

Product 1

HCID 15550516HCID 15550516, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

The compound (5.13 g) of Example 1 was dissolved into DMF (70 ml) and, after adding sodium hydride (1.00 g), the mixture was stirred for 1 hour at room temperature. This was cooled in ice bath and ethyl 2-bromoacetate (2.77 ml) was added. After stirring for 18 hours until the temperature rose to room temperature, saturated aqueous solution of ammonium chloride was added and diluted with water, which was extracted with ether. After the organic layer was washed with water and with saturated brine and dried over anhydrous sodium sulfate, solvent was distilled off under reduced pressure. The residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:2) to obtain aimed product (4.63 g) as a yellow oily product.

Workup

  1. temperatureThis was cooled in ice bath
  2. stirringAfter stirring for 18 hours until the temperature
  3. customrose to room temperature
  4. extractionwas extracted with ether
  5. washAfter the organic layer was washed with water and with saturated brine
  6. dry with materialdried over anhydrous sodium sulfate, solvent
  7. distillationwas distilled off under reduced pressure
  8. customThe residue was purified by means of silica gel column chromatography (developing solvent, ethyl acetate:n-hexane=1:2)

Sources & evidence

ORD record
ord-98a97435e27e4f06a22a2bd6d132a701
Source dataset
uspto-grants-2001_07
Patent number
US06265577B1

Reaction notes

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