(2R,5S)-6-(benzyloxy)-7-oxo-N'-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide → (2R,5S)-6-hydroxy-7-oxo-N'-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide

HRID 1053446Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1053446
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@@H:10]1[CH2:11][CH2:12][C@@H:13]2[C:18]([NH:20][NH:21][C:22](=[O:28])[CH2:23][C:24]([F:27])([F:26])[F:25])=[O:19])C1C=CC=CC=1.[H][H]>CO.[Pd]>[OH:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@@H:10]1[CH2:11][CH2:12][C@@H:13]2[C:18]([NH:20][NH:21][C:22](=[O:28])[CH2:23][C:24]([F:27])([F:25])[F:26])=[O:19]

Komponenten

5

Edukt 2

HCID 86694061(2R,5S)-6-(benzyloxy)-7-oxo-N'-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 86694062(2R,5S)-6-hydroxy-7-oxo-N'-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazideAusbeute 94,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of (2R,5S)-6-(benzyloxy)-7-oxo-N′-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 229 (0.26 g, 0.65 mml) in methanol (20 mL) was added 5% Pd/C (0.30 g). The mixture was hydrogenated under 10 psi hydrogen atmosphere at room temperature for 1 h. The catalyst was filtered out through Celite, and the filtrate was evaporated to give (2R,5S)-6-hydroxy-7-oxo-N′-(3,3,3-trifluoropropanoyl)-1,6-diazabicyclo[3.2.1]octane-2-carbohydrazide 230 (0.19 g, 93.6%) as a colorless foam.

Aufarbeitung

  1. filtrationThe catalyst was filtered out through Celite
  2. customthe filtrate was evaporated

Quellen und Nachweise

ORD-Eintrag
ord-010fc983676640e2a0ad8f210866f2d6
Quelldatensatz
uspto-grants-2016_07
Patentnummer
US09393239B2

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