Ethyl Acetate → 3-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid Ethyl Ester

HRID 11656

Reaction equation

HRID 11656 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:10][CH2:11][C:12]([N:14]2[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]3[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=3)[CH2:16][C@H:15]2[CH3:29])=[O:13])=[C:6]([CH:9]=1)[CH:7]=O.C(=O)([O-])[O-].[K+].[K+].[C:36]([O:39][CH2:40][CH3:41])(=[O:38])[CH3:37]>C(O)C>[CH2:40]([O:39][C:36](=[O:38])[CH:37]=[CH:7][C:6]1[CH:9]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[O:10][CH2:11][C:12]([N:14]1[CH2:19][C@H:18]([CH3:20])[N:17]([CH2:21][C:22]2[CH:23]=[CH:24][C:25]([F:28])=[CH:26][CH:27]=2)[CH2:16][C@H:15]1[CH3:29])=[O:13])[CH3:41]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 53673807(2R,5S)-5-Chloro-2-{2-[4-(4-fluoro-benzyl)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde

Product 1

HCID 696554333-(5-Chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-phenyl)-acrylic Acid Ethyl Ester

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-chloro-2-{2-[4-(4-fluoro-benzyl)-(2R,5S)-2,5-dimethyl-piperazin-1-yl]-2-oxo-ethoxy}-benzaldehyde (0.50 g, 1.19 mmol) in ethanol (10 mL) at 0° C. was added potassium carbonate (0.4 mL, 2.4 mmol, 6 M solution in water) and triethyl phosphonoacetate (0.47 mL, 2.4 mmol). The reaction was stirred at 0° C. for 2 hours, then at ambient temperature 12 hours. The reaction was diluted with ethyl acetate and filtered through a pad of celite. The filtrate was then washed with saturated aqueous sodium hydrogen carbonate and brine. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. The crude product was purified by chromatography on silica gel to give the title compound (0.51 g)

Workup

  1. customat ambient temperature
  2. custom12 hours
  3. filtrationfiltered through a pad of celite
  4. washThe filtrate was then washed with saturated aqueous sodium hydrogen carbonate and brine
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude product was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-ece4c6e842f64e08ab10c24ffc71a829
Source dataset
uspto-grants-2006_08
Patent number
US07098212B2

Linked notes

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