HCID 178487800, Verbindung → HCID 178487794, Verbindung

HRID 1422915Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1422915
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-cyclohexyl)-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-200238c8280a480e96daf5e12eabf83e
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927541B2

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