Citric Acid → HCID 58044110, Verbindung

HRID 626760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 626760
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]2[CH:13]=[N:14][C:15]([N:18]=C(C3C=CC=CC=3)C3C=CC=CC=3)=[CH:16][CH:17]=2)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C1COCC1>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH:10]([C:12]2[CH:13]=[N:14][C:15]([NH2:18])=[CH:16][CH:17]=2)[CH2:11]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 2

HCID 311Citric AcidHCID 86697066tert-Butyl 3-(6-(Diphenylmethyleneamino)pyridin-3-yl)azetidine-1-carboxylate

Produkt 1

HCID 58044110HCID 58044110, VerbindungAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of 3-[6-(benzhydrylideneamino)-pyridin-3-yl]-azetidine-1-carboxylic acid tert-butyl ester (400 mg, 0.97 mmol) in THF (20 mL) was added citric acid (10 mL, 10% aqueous) and the reaction mixture was stirred at room temperature overnight. The resultant mixture was quenched by adding sodium hydrogen carbonate solution and was then extracted with ethyl acetate (×2). The combined organic washings were washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (70-100% ethyl acetate in cyclohexane) to afford the title compound as a white solid (183 mg, 76%). LCMS (Method C): RT=1.85 min, m/z: 250 [M+H+].

Aufarbeitung

  1. customThe resultant mixture was quenched
  2. additionby adding sodium hydrogen carbonate solution
  3. extractionwas then extracted with ethyl acetate (×2)
  4. washThe combined organic washings were washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel flash chromatography (70-100% ethyl acetate in cyclohexane)

Quellen und Nachweise

ORD-Eintrag
ord-994071239e724523b840f6ce4850fd25
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309240B2

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