tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate → HCID 117622711, Verbindung

HRID 56874Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 56874
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]#[N:33])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([C:16](=[CH:24][C:25]3([CH2:29][CH3:30])[CH2:28][O:27][CH2:26]3)[C:17]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:18])[C:10](=[O:31])[CH:9]=2)[CH:7]=1>[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:32]#[N:33])=[C:6]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][N:11]([CH:16]([CH2:24][C:25]3([CH2:29][CH3:30])[CH2:26][O:27][CH2:28]3)[C:17]([O:19][C:20]([CH3:21])([CH3:23])[CH3:22])=[O:18])[C:10](=[O:31])[CH:9]=2)[CH:7]=1

Komponenten

3

Edukt 1

HCID 118877902tert-Butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate

Produkt 1

HCID 117622711HCID 117622711, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 25517Ammonium ChlorideLösungsmittel

Versuchsvorschrift

At RT, 302 mg (641 μmol) of tert-butyl 2-[4-(5-chloro-2-cyanophenyl)-5-methoxy-2-oxopyridin-1(2H)-yl]-3-(3-ethyloxetan-3-yl)prop-2-enoate (isomer mixture) were admixed with 20 ml of a “Hot Stryker's” reagent solution [B. A. Baker et al. Org. Lett. 2008, 10, 289-292]. The reaction mixture was stirred at RT for 1.5 h, and 20 ml of saturated aqueous ammonium chloride solution were then added. After phase separation, the aqueous phase was extracted three times with 25 ml of ethyl acetate. The combined organic phases were dried over magnesium sulphate and filtered, and the solvent was removed under reduced pressure. The residue was purified by flash chromatography (120 g silica cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient). Yield: 275 mg (91% of theory)

Aufarbeitung

  1. customAt RT
  2. customAfter phase separation
  3. extractionthe aqueous phase was extracted three times with 25 ml of ethyl acetate
  4. dry with materialThe combined organic phases were dried over magnesium sulphate
  5. filtrationfiltered
  6. customthe solvent was removed under reduced pressure
  7. customThe residue was purified by flash chromatography (120 g silica cartridge, 85 ml/min, cyclohexane/ethyl acetate gradient)

Quellen und Nachweise

ORD-Eintrag
ord-de808c8ef73647fda2f4c448aee70f9d
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09434690B2

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