Ethyl bromoacetate → HCID 71254753, compound

HRID 714492Notes

Reaction equation

HRID 714492 reaction equation
[CH:1]1[C:6]([C@H:7]2[O:16][C:15]3[CH:14]=[C:13]([OH:17])[CH:12]=[C:11]([OH:18])[C:10]=3[CH2:9][C@H:8]2[OH:19])=[CH:5][C:4]([OH:20])=[C:3]([OH:21])[CH:2]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]>CN(C=O)C.C(OCC)(=O)C>[OH:21][C:3]1[CH:2]=[CH:1][C:6]([C@@H:7]2[C@H:8]([OH:19])[CH2:9][C:10]3[C:15](=[CH:14][C:13]([OH:17])=[CH:12][C:11]=3[OH:18])[O:16]2)=[CH:5][C:4]=1[O:20][CH2:29][C:30]([O:32][CH2:33][CH3:34])=[O:31]

Participants

6

Reactant 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 72276(-)-Epicatechin

Product 1

HCID 71254753HCID 71254753, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (−)-epicatechin (1.16 g, 4 mmol) and potassium carbonate (1.1 g, 8 mmol) in DMF (10 mL) at −20° C. was added ethyl bromoacetate (490 mL, 4.4 mmol). The reaction was stirred at the same temperature for 2 hr, allowed to warm to RT, and stirred for 2 hr. The reaction was diluted with ethyl acetate, washed with citric acid then brine, dried over sodium sulfate, and concentrated. The residue was purified by preparative reverse phase HPLC using a gradient of 10% to 80% acetonitrile/(0.2% formic acid/water) over 20 min, analyzing at 280 nm. The appropriate fractions were frozen and lyophilized to give as white powders:

Workup

  1. stirringstirred for 2 hr
  2. washwashed with citric acid
  3. dry with materialbrine, dried over sodium sulfate
  4. concentrationconcentrated
  5. customThe residue was purified by preparative reverse phase HPLC
  6. customover 20 min
  7. temperatureThe appropriate fractions were frozen
  8. customto give as white powders

Sources & evidence

ORD record
ord-add792c4336a467db710deeee542dc6c
Source dataset
uspto-grants-2015_11
Patent number
US09187448B2

Reaction notes

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