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Potassium Carbonate → (7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723391
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 723391
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:23])=[C:16]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([O:29]C(=O)C(C)(C)C)[C@H:5]1[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1)(=O)C.C(=O)([O-])[O-].[K+].[K+]>NC(O)C>[C:17]1([C:16]2[N:11]3[CH:10]=[CH:9][C:8]4[C@@H:7]([O:24][CH2:25][CH2:26][O:27][CH3:28])[C@H:6]([OH:29])[C@@H:5]([C:36]5[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=5)[NH:4][C:13]=4[C:12]3=[N:14][C:15]=2[CH3:23])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
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Komponenten

4

Edukt 2

HCID 11430Potassium CarbonateHCID 69586312(7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Produkt 1

HCID 11304956(7R,8R,9R)-3,9-Diphenyl-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 522583Acetaldehyde ammoniaLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 1.14 g (2.05 mmol) of (7R,8R,9R)-10-acetyl-3,9-diphenyl-7-(2-methoxyethoxy)-2-methyl-8-pivaloyloxy-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine and 2.28 g (16.5 mmol) potassium carbonate in aminoethanol is stirred at 60° C. for 4 h. The reaction is quenched by adding of saturated aqueous ammonium chloride solution. Subsequently the mixture is extracted twice with ethyl acetate. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3) to give 0.52 g (1.21 mmol/60%) of the title compound as a colourless solid with a melting point of 190–192° C. (diethyl ether).

Aufarbeitung

  1. customThe reaction is quenched
  2. additionby adding of saturated aqueous ammonium chloride solution
  3. extractionSubsequently the mixture is extracted twice with ethyl acetate
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (diethyl ether/petrol ether: 7/3)

Quellen und Nachweise

ORD-Eintrag
ord-6abd21351a764ff39d10a9b922d64dda
Quelldatensatz
uspto-grants-2006_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07141567B2

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