Ethyl bromoacetate → HCID 67096604, compound

HRID 492239Notes

Reaction equation

HRID 492239 reaction equation
[NH2:1][CH:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28]>O1CCOCC1>[CH2:30]([O:29][C:27](=[O:28])[CH3:26])[CH3:31].[CH2:12]([N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:2]1[NH2:1])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 10681402HCID 10681402, compound

Product 1

HCID 67096604HCID 67096604, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of compound 24 (400 mg, 1.68 mmol) in dioxane (5 mL) was added potassium carbonate (695 mg, 5.04 mmol) and ethyl bromoacetate (0.56 mL, 5.04 mmol) and the resulting reaction mixture is allowed to stir at reflux for 18 hours. The reaction mixture is poured onto water and extracted with ethyl acetate (3×20 mL). The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and concentrated in vacuo. Chromatography (SiO2, 40% EtOAc-Hexanes eluant) provided 300 mg of 25 as a yellow oil (546 mg theoretical, 55% yield).

Workup

  1. customthe resulting reaction mixture
  2. temperatureat reflux for 18 hours
  3. additionThe reaction mixture is poured onto water
  4. extractionextracted with ethyl acetate (3×20 mL)
  5. dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-700dbc3d136148ac905e3c09476577bc
Source dataset
uspto-grants-2009_05
Patent number
US07531671B2

Reaction notes

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