tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate → tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate

HRID 627240Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627240
C([O:8][N:9]1[C:15](=[O:16])[N:14]2[CH2:17][C@H:10]1[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[CH:12][C@H:13]2[C:18](=[O:20])[NH2:19])C1C=CC=CC=1>CCOC(C)=O.[Pd]>[C:18]([C@@H:13]1[CH:12]=[C:11]([CH2:21][CH2:22][NH:23][C:24](=[O:30])[O:25][C:26]([CH3:27])([CH3:28])[CH3:29])[C@@H:10]2[CH2:17][N:14]1[C:15](=[O:16])[N:9]2[OH:8])(=[O:20])[NH2:19]

Komponenten

4

Edukt 1

HCID 89852204tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate2×

Produkt 1

HCID 117940260tert-butyl 2-((2S,5R)-2-carbamoyl-6-hydroxy-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of tert-butyl 2-((2S,5R)-6-(benzyloxy)-2-carbamoyl-7-oxo-1,6-diazabicyclo[3.2.1]oct-3-en-4-yl)ethylcarbamate (Intermediate 227, 0.300 g, 0.72 mmol) in EtOAc (5 mL) was added 10% Pd/C (0.077 g, 0.72 mmol). The reaction mixture was stirred under hydrogen for 30 minutes. The reaction mixture was filtered through celite and washed with EtOAc. The solvent was removed in vacuo to give the title compound as a white solid (0.23 g, 98%).

Aufarbeitung

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with EtOAc
  3. customThe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-3226fa1876a445bbbe3ad8e1a9561a21
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309245B2

Notizen zur Reaktion

Wird geladen…