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Hydrochloric Acid → HCID 178499132, Verbindung

HRID 869728
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 869728
C(OC([NH:8][C@H:9]([C:11]([NH:13][C@@H:14]([C:19](=O)[CH3:20])[C:15]([O:17][CH3:18])=[O:16])=[O:12])[CH3:10])=O)(C)(C)C.Cl>O1CCOCC1>[OH:12][C:11]1[N:13]=[C:14]([C:15]([O:17][CH3:18])=[O:16])[C:19]([CH3:20])=[N:8][C:9]=1[CH3:10]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 313Hydrochloric AcidHCID 86674523methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate

Produkt 1

HCID 178499132HCID 178499132, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 312751,4-DioxaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A solution of methyl (2S)-2-{[N-(tert-butoxycarbonyl)-L-alanyl]amino}-3-oxobutanoate (3.05 g, 10.1 mmol) and 4N hydrochloric acid in 1,4-dioxane (10 mL) was stirred at room temperature. After being stirred for 1 h at same temperature, the reaction mixture was concentrated in vacuo. A solution of the residue in pyridine (50 mL) was heated at 60° C. for 4 h. After being cooled to ambient temperature, the mixture was concentrated in vacuo. The residue was poured into water, and the mixture was extracted with dichloromethane. The organic layer was washed with saturated brine, dried over magnesium sulfate, filtrated and concentrated in vacuo. The residue was triturated with hexane-ethyl acetate (1:1) to give methyl 6-hydroxy-3,5-dimethylpyrazine-2-carboxylate. MS (APCI): m/z 183 (M+H).

Aufarbeitung

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. temperatureAfter being cooled to ambient temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was poured into water
  5. extractionthe mixture was extracted with dichloromethane
  6. washThe organic layer was washed with saturated brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated in vacuo
  10. customThe residue was triturated with hexane-ethyl acetate (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-08c8b399f72e42feab2cd18ef302586f
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08969376B2

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