Water → HCID 59556934, compound

HRID 1173589Notes

Reaction equation

HRID 1173589 reaction equation
[CH2:1]([N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C@@H:9]([CH3:18])[C:10](=[O:17])[CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:27][CH2:28]Br.C(=O)([O-])[O-].[K+].[K+].O>CC(C)=O>[CH2:1]([N:8]([CH2:19][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[CH:9]([CH3:18])[C:10]([C:11]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH2:28][CH2:27]1)=[O:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 67104986HCID 67104986, compound

Product 1

HCID 59556934HCID 59556934, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of ethyl(4S)-4-(dibenzylamino)-3-oxopentanoate (500 mg) synthesized according to the method described in Journal of Organic Chemistry, vol. 62, pp. 2292-2297 (1997), 1,2-dibromoethane (0.19 mL) and potassium carbonate (405 mg) in acetone (15 mL), was stirred under reflux overnight. The reaction mixture was added to water, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→2/1) to give the title compound as a colorless oil (yield: 231.4 mg, 43.0%).

Workup

  1. temperatureunder reflux overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=1/0→2/1)

Sources & evidence

ORD record
ord-d5cab465c8254eefab2ab242ab5da8c0
Source dataset
uspto-grants-2010_11
Patent number
US07834051B2

Reaction notes

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