HCID 178487960, Verbindung → HCID 178487969, Verbindung

HRID 633804Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 633804
[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]1[CH2:13][CH2:12][C@H:11]([CH2:14][CH:15]2[CH:19]([C:20]3[C:29]4[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=4)[N:23]=[CH:22][C:21]=3[O:32]CC3C=CC=CC=3)OC(=O)[O:16]2)[CH2:10][CH2:9]1)([CH3:4])([CH3:3])[CH3:2]>[Pd].CO.C(N(CC)CC)C>[C:1]([O:5][C:6](=[O:41])[NH:7][C@H:8]1[CH2:9][CH2:10][C@H:11]([CH2:14][CH:15]([OH:16])[CH2:19][C:20]2[C:29]3[C:24](=[CH:25][CH:26]=[C:27]([O:30][CH3:31])[N:28]=3)[N:23]=[CH:22][C:21]=2[OH:32])[CH2:12][CH2:13]1)([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 1

HCID 178487960HCID 178487960, Verbindung

Produkt 1

HCID 178487969HCID 178487969, VerbindungAusbeute 68,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 8471TriethylamineKatalysatorHCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

10% Palladium on activated carbon (976 mg, 0.91 mmol, 0.3 eq) is added at room temperature to a stirred solution of {trans-4-[5-(3-benzyloxy-6-methoxy-[1,5]naphthyridin-4-yl)-2-oxo-[1,3]dioxolan-4-ylmethyl]-cyclohexyl}-carbamic acid tert-butyl ester (1.70 g, 3.02 mmol, 1.0 eq) in methanol (200 mL), followed by several drops of triethylamine. The resulting mixture is stirred under hydrogen flow (1 bar) at room temperature for 1 hour. The catalyst is then removed by filtration and the solution is concentrated to afford {trans-4-[2-hydroxy-3-(3-hydroxy-6-methoxy-[1,5]naphthyridin-4-yl)-propyl]-cyclohexyl}-carbamic acid tert-butyl ester as a white solid (890 mg, 68% yield).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-7b7c7c77ef0a4dddb1656f4a9c7d5065
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09321788B2

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