HCID 178487800, Verbindung → HCID 178487794, Verbindung

HRID 2273204Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2273204
C(O[CH:5]1[C:18]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH3:20])[CH:16]=3)[N:11]=[CH:10][C:9]=2[O:8][CH:7]([O:21][C:22](=[O:24])[CH3:23])[CH:6]1[C@H:25]1[CH2:30][CH2:29][C@H:28]([NH:31][C:32]([O:34][C:35]([CH3:38])([CH3:37])[CH3:36])=[O:33])[CH2:27][CH2:26]1)(=O)C>[Pd].CO>[C:35]([O:34][C:32]([NH:31][C@H:28]1[CH2:27][CH2:26][C@H:25]([CH:6]2[CH2:5][C:18]3[C:17]4[C:12](=[CH:13][CH:14]=[C:15]([O:19][CH3:20])[CH:16]=4)[N:11]=[CH:10][C:9]=3[O:8][CH:7]2[O:21][C:22](=[O:24])[CH3:23])[CH2:30][CH2:29]1)=[O:33])([CH3:38])([CH3:36])[CH3:37]

Komponenten

4

Edukt 1

HCID 178487800HCID 178487800, Verbindung

Produkt 1

HCID 178487794HCID 178487794, VerbindungAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

10% Palladium on activated carbon (500 mg, 4.70 mmol, 1.09 eq) is added at room temperature to a stirred solution of acetic acid 4-acetoxy-3-(trans-4-tert-butoxycarbonylamino-cyclo hexyl)-6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-2-yl ester (2.3 g, 4.29 mmol, 1.0 eq) in methanol (60 mL). The reaction mixture is stirred at room temperature under hydrogen flow (10 bars) for 72 hours. The catalyst is then removed by filtration and the solution is concentrated to afford acetic acid 3-(trans-4-tert-butoxycarbonylamino-cyclohexyl)-6-methoxy-3,4-dihydro-2H-1-oxa-9-aza-phenanthren-2-yl ester as a yellow semisolid (1.45 g, 71% yield) which is directly engaged in the next step.

Aufarbeitung

  1. customThe catalyst is then removed by filtration
  2. concentrationthe solution is concentrated

Quellen und Nachweise

ORD-Eintrag
ord-e684fad106ef4540b1fdb396f7666eec
Quelldatensatz
uspto-grants-2015_09
Patentnummer
US09120822B2

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