Phosphorus oxychloride → HCID 59006363, Verbindung

HRID 2378944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378944
[C:1]([C:4]1[NH:5][C:6](=[O:22])[N:7]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[CH:8]=1)(=O)[NH2:2].P(Cl)(Cl)(Cl)=O>N1C=CC=CC=1>[C:1]([C:4]1[NH:5][C:6](=[O:22])[N:7]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:20])([CH3:19])[CH3:21])=[O:16])[CH2:13][CH2:14]2)[CH:8]=1)#[N:2]

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 59006367Tert-butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate

Produkt 1

HCID 59006363HCID 59006363, VerbindungAusbeute 29 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

tert-Butyl 4-(4-carbamoyl-2-oxo-2,3-dihydroimidazol-1-yl)piperidine-1-carboxylate (175 mg, 0.564 mmol) was suspended in pyridine (3.0 mL). Phosphorus oxychloride (53 μL, 0.569 mmol) was added to the mixture drop-wise. Mixture stirred at ambient temperature for 30 minutes. Reaction was quenched with the drop-wise addition of water. Material was extracted twice with ethyl acetate and the aqueous phase was discarded. Material was washed successively with 1N hydrochloric acid brine and the aqueous phases were discarded. Organics were dried MgSO4, filtered and then concentrated to dryness. Silica gel chromatography eluting ethyl acetate-hexanes afforded the title compound as white solid in 29% yield. MS (M−H)−=291.1.

Aufarbeitung

  1. customReaction
  2. customwas quenched with the drop-wise addition of water
  3. extractionMaterial was extracted twice with ethyl acetate
  4. washMaterial was washed successively with 1N hydrochloric acid brine
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. washSilica gel chromatography eluting ethyl acetate-hexanes

Quellen und Nachweise

ORD-Eintrag
ord-094d336955f04a5494511153c0937b2b
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470680B2

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