Ethyl bromopyruvate → HCID 15233869, compound

HRID 861986Notes

Reaction equation

HRID 861986 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][P:9](=[O:16])([O:13][CH2:14][CH3:15])[O:10][CH2:11][CH3:12])[CH:5]=[CH:4][N:3]=1.Br[CH2:18][C:19](=O)[C:20]([O:22][CH2:23][CH3:24])=[O:21]>COCCOC>[CH2:14]([O:13][P:9]([CH2:8][C:6]1[CH:5]=[CH:4][N:3]2[CH:18]=[C:19]([C:20]([O:22][CH2:23][CH3:24])=[O:21])[N:1]=[C:2]2[CH:7]=1)([O:10][CH2:11][CH3:12])=[O:16])[CH3:15]

Participants

4

Reactant 2

HCID 66144Ethyl bromopyruvateHCID 86752042HCID 86752042, compound

Product 1

HCID 15233869HCID 15233869, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

The product from Example 16 (0.87 g, 3.56 mmol) was dissolved in DME (25 mL) and placed in a 100 mL flask. Ethyl bromopyruvate (0.76 g, 3.92 mmol) was added to the flask, and the reaction was allowed to stir under a N2 atmosphere for 16 h. After solvent removal in vacuo, the residue was taken up in abs EtOH (25 mL) and refluxed for 5 h. The reaction was cooled to room temperature and solvent was removed in vacuo. The residue was dissolved in aqueous K2CO3 and the product extracted with EtOAc. Purification via a chromatotron (97/2/1 CH2Cl2 /EtOH/NH4OH) produced 0.38 g (32%) of title compound.

Workup

  1. customplaced in a 100 mL flask
  2. customAfter solvent removal in vacuo
  3. temperaturerefluxed for 5 h
  4. customsolvent was removed in vacuo
  5. dissolutionThe residue was dissolved in aqueous K2CO3
  6. extractionthe product extracted with EtOAc
  7. customPurification via a chromatotron (97/2/1 CH2Cl2 /EtOH/NH4OH)

Sources & evidence

ORD record
ord-4ecc9c2d34a4400e9dc81744d0fd9145
Source dataset
uspto-grants-1998_02
Patent number
US05716964

Reaction notes

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