Hydrochloric Acid → (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one

HRID 898251Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 898251
C(=O)([O:5][C:6]1[CH:11]=[CH:10][C:9]([S:12]([N:15]2[C:24]3[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=3)[NH:18][C:17](=[O:26])[C@@H:16]2[CH2:27][CH3:28])(=[O:14])=[O:13])=[CH:8][CH:7]=1)OCC.C(=O)([O-])[O-].[Cs+].[Cs+].I[CH2:37][CH2:38][CH3:39].[OH-].[Na+].Cl>CC(C)=O>[CH2:27]([C@@H:16]1[N:15]([S:12]([C:9]2[CH:10]=[CH:11][C:6]([OH:5])=[CH:7][CH:8]=2)(=[O:14])=[O:13])[C:24]2[C:19](=[CH:20][CH:21]=[C:22]([F:25])[CH:23]=2)[N:18]([CH2:37][CH2:38][CH3:39])[C:17]1=[O:26])[CH3:28]

Komponenten

7

Edukt 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 14798Sodium HydroxideHCID 336431-IodopropaneHCID 69224101ethyl 4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate

Produkt 1

HCID 11538398(3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-oneAusbeute 30,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 180AcetoneLösungsmittel

Reaktionsbedingungen

Temperatur
62 °C

Versuchsvorschrift

To a solution of ethyl 4-{[(2S)-2-ethyl-7-fluoro-3-oxo-3,4-dihydroquinoxalin-1(2H)-yl]sulfonyl}phenyl carbonate (0.35 g, 0.83 mmol) in acetone (5 mL) was added cesium carbonate (0.3 g, 0.91 mmol), and 1-iodopropane (0.32 ml, 3.32 mmol). The mixture was heated at 62° C. for 2.5 hours, cooled to 25° C., and treated with a 2N aqueous solution of sodium hydroxide (3 mL). The reaction was then stirred at 25° C. for 2 hours, and was acidified to pH<2 with the addition of a 2N aqueous solution of hydrochloric acid. The resulting mixture was partitioned between ethyl acetate and a saturated aqueous solution of sodium chloride. The organic layer was separated, dried over magnesium sulfate, and concentrated. The product was purified via flash column chromatography (SiO2, 30% ethyl acetate:hexane eluted to 60% ethyl acetate:hexane) to afford 0.1 g (3S)-3-ethyl-6-fluoro-4-[(4-hydroxyphenyl)sulfonyl]-1-propyl-3,4-dihydroquinoxalin-2(1H)-one as a white solid. MS (ESI) m/z 393 ([M+H]+); MS (ESI) m/z 391 ([M−H]−); Anal. Calcd for C19H21FN2O4S: C, 58.15; H, 5.39; N, 7.14. Found: C, 57.95; H, 5.46; N, 6.66.

Aufarbeitung

  1. temperaturecooled to 25° C.
  2. customThe resulting mixture was partitioned between ethyl acetate
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe product was purified via flash column chromatography (SiO2, 30% ethyl acetate:hexane eluted to 60% ethyl acetate:hexane)

Quellen und Nachweise

ORD-Eintrag
ord-abe54c9b8f254840b370f598eb337471
Quelldatensatz
uspto-grants-2008_04
Patentnummer
US07351709B2

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