Sodium Carbonate → HCID 67960066, Verbindung

HRID 1773776Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1773776
C(OC([C:6]1[N:7]([CH2:19][CH:20]([NH:22][C:23]([O:25]C(C)(C)C)=O)[CH3:21])[N:8]=[C:9]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[CH:10]=1)=O)C.C([O-])([O-])=O.[Na+].[Na+]>Cl.O1CCOCC1.C(Cl)Cl>[CH3:21][CH:20]1[CH2:19][N:7]2[N:8]=[C:9]([CH2:11][O:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:10]=[C:6]2[C:23](=[O:25])[NH:22]1

Komponenten

6

Edukt 2

HCID 10340Sodium CarbonateHCID 67958408ethyl 1-{2-[(tert-butoxycarbonyl)amino]propyl}-3-(phenoxymethyl)-1H-pyrazole-5-carboxylate

Produkt 1

HCID 67960066HCID 67960066, VerbindungAusbeute 106,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 312751,4-DioxaneLösungsmittel

Versuchsvorschrift

Rac-2-(2-tert-butoxycarbonylamino-propyl)-5-phenoxymethyl-2H-pyrazole-3-carboxylic acid ethyl ester (5.58 g, 5.53 mmol, 40% pure) was dissolved in a 4N solution of HCl in 1,4-dioxane (40 mL) under N2 at 0° C. The mixture was stirred at room temperature for 3 hours. The mixture was basified with a saturated solution of Na2CO3 and the mixture stirred at room temperature for 3 days. Then the mixture was diluted with DCM. The organic layer was separated, dried (Na2SO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 70/30). The desired fractions were collected and the solvents evaporated in vacuo to yield rac-6-methyl-2-phenoxymethyl-6,7-dihydro-5H-pyrazolo[1,5-a]pyrazin-4-one (1.52 g, 91% yield) as a white solid.

Aufarbeitung

  1. stirringthe mixture stirred at room temperature for 3 days
  2. customThe organic layer was separated
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 70/30)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-654c5550ed6f4c969b242eb34f2b601f
Quelldatensatz
uspto-grants-2016_02
Patentnummer
US09255103B2

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