HCID 86667468, compound → HCID 56832870, compound

HRID 2401910Notes

Reaction equation

HRID 2401910 reaction equation
Cl[CH:2]([C:8](=O)[CH2:9][C:10]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][CH:11]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[N:18]1([C:24](=[Se:26])[NH2:25])[CH2:23][CH2:22][O:21][CH2:20][CH2:19]1>C(O)(C)C>[Cl:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][C:8]2[N:25]=[C:24]([N:18]3[CH2:23][CH2:22][O:21][CH2:20][CH2:19]3)[Se:26][C:2]=2[C:3]([O:5][CH2:6][CH3:7])=[O:4])=[CH:11][CH:12]=1

Participants

4

Reactant 2

HCID 86667468HCID 86667468, compoundHCID 178514153HCID 178514153, compound

Product 1

HCID 56832870HCID 56832870, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

In a round bottomed flask were placed ethyl 2-chloro-4-(4-chlorophenyl)-3-oxobutanoate (84.4 mg, 0.3069 mmol), isopropyl alcohol (5 mL), and morpholine-4-carboselenoamide (80.0 mg, 0.414 mmol). The resulting mixture was brought to reflux under an atmosphere of nitrogen (all solids dissolved to give a clear pale pink solution). After ˜1 hour reflux, TLC analysis indicated that all starting materials had been consumed with the production of one major product. The reaction was allowed to cool to room temperature and stir overnight. The solvent was removed on the rotovap then the residue was dissolved in minimal dichloromethane and purified by column chromatography on silica gel (gradient 100% hexane to 35% ethyl acetate) to afford 35 mg (28% yield) product as a white solid. LC/MS (FA) ES+ 413/415/417. 1H NMR (400 MHz, DMSO) δ 7.37-7.23 (m, 4H), 4.25-4.14 (m, 4H), 3.72-3.62 (t, J=4.9 Hz, 4H), 3.50-3.41 (t, J=4.8 Hz, 4H), 1.27-1.20 (t, J=7.1 Hz, 3H).

Workup

  1. customIn a round bottomed flask were placed
  2. temperatureto reflux under an atmosphere of nitrogen (all solids
  3. dissolutiondissolved
  4. customto give a clear pale pink solution)
  5. temperatureAfter ˜1 hour reflux
  6. customhad been consumed with the production of one major product
  7. customThe solvent was removed on the rotovap
  8. dissolutionthe residue was dissolved in minimal dichloromethane
  9. custompurified by column chromatography on silica gel (gradient 100% hexane to 35% ethyl acetate)

Sources & evidence

ORD record
ord-27bbd56ca88646edb1882d836f639010
Source dataset
uspto-grants-2014_08
Patent number
US08796268B2

Reaction notes

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