Ethyl bromopyruvate → HCID 66797364, Verbindung

HRID 1916884

Reaktionsgleichung

Reaktionsgleichung von HRID 1916884
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[NH:20])[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])([CH3:12])[CH3:11])=[CH:4][CH:3]=1.C([O-])(O)=O.[Na+].Br[CH2:27][C:28](=O)[C:29]([O:31][CH2:32][CH3:33])=[O:30]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:27]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[N:20]=[C:9]2[C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[F:19])([CH3:12])[CH3:11])=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 66144Ethyl bromopyruvateHCID 516892Sodium BicarbonateHCID 178449870HCID 178449870, Verbindung

Produkt 1

HCID 66797364HCID 66797364, VerbindungAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
70 °C

Versuchsvorschrift

To a 250 mL round bottom flask attached with condenser was added N-(4-bromophenyl)-2-(2-fluorophenyl)-2-methylpropanimidamide (5.0 g, 15 mmol), anhydrous THF (80 mL), NaHCO3 (2.52 g, 30 mmol), and 90% ethyl bromopyruvate (1.90 mL, 15.1 mmol). The reaction mixture was stirred at 70° C. for 2 hr prior to analysis by LCMS. The cooled reaction mixture was decanted and concentrated in vacuo. The residue was taken into toluene (65 mL) and acetic acid (1.8 mL). The solution was stirred at reflux for 1 hr. The cooled solution was washed with H2O (150 mL×3), dried over Na2SO4, filtered, concentrated in vacuo, and chromatographed through a SiO2 column using a 100% Hx to 70% EtOAc gradient to afford purified title compound (4.3 g, 67% yield). LCMS (ES): m/z=431.3, 433.3 [M+H]+.

Aufarbeitung

  1. customTo a 250 mL round bottom flask attached with condenser
  2. customThe cooled reaction mixture
  3. customwas decanted
  4. concentrationconcentrated in vacuo
  5. stirringThe solution was stirred
  6. temperatureat reflux for 1 hr
  7. washThe cooled solution was washed with H2O (150 mL×3)
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customchromatographed through a SiO2 column
  12. customto afford

Quellen und Nachweise

ORD-Eintrag
ord-264c1cae779945cca665dd7bd7d1dd25
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08618154B2

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