Sulfuric Acid → (7R,8R,9R)-2,3-Dimethyl-8-hydroxy-7-(2-hydroxyethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 723390Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 723390
[OH:1][C@@H:2]1[C:11]2[CH:10]=[CH:9][N:8]3[C:12]([CH3:16])=[C:13]([CH3:15])[N:14]=[C:7]3[C:6]=2[NH:5][C@H:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C@H:3]1[OH:23].S(=O)(=O)(O)O.[OH-].[Na+].C[O:32][CH2:33][CH2:34]O>>[CH3:15][C:13]1[N:14]=[C:7]2[C:6]3[NH:5][C@H:4]([C:17]4[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=4)[C@@H:3]([OH:23])[C@H:2]([O:1][CH2:34][CH2:33][OH:32])[C:11]=3[CH:10]=[CH:9][N:8]2[C:12]=1[CH3:16]

Komponenten

5

Edukt 4

HCID 1118Sulfuric AcidHCID 80192-MethoxyethanolHCID 14798Sodium HydroxideHCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

Produkt 1

HCID 10193645(7R,8R,9R)-2,3-Dimethyl-8-hydroxy-7-(2-hydroxyethoxy)-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reaktionsbedingungen

Temperatur
55 °C

Versuchsvorschrift

To a suspension of 2.00 g (6.40 mmol) (7R,8R,9R)-7,8-Dihydroxy-2,3-dimethyl-9-phenyl-7.8.9.10-tetrahydroimidazo[1.2-h][1.7]naphthyridine in 2-methoxyethanol (100 ml) is added 1.26 g (12.8 mmol) sulfuric acid and the mixture is stirred for 3 h at 55° C. Subsequently the reaction is poured out into a of 0° C. cooled aqueous solution of sodium hydroxide (2N). The mixture is extracted with dichloromethane two times. The combined organic layer are washed with water four times, dried over sodium sulfate and concentrated in vacuo. The crude product is purified by column chromatography (diethyl ether/2-propanol: 10/1) to give 0.35 g (0.99 mmol/16%) of the title compound as a colourless solid with a melting point of 107–109° C. (diethyl ether).

Aufarbeitung

  1. additionSubsequently the reaction is poured out into a of 0° C.
  2. extractionThe mixture is extracted with dichloromethane two times
  3. washThe combined organic layer are washed with water four times
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product is purified by column chromatography (diethyl ether/2-propanol: 10/1)

Quellen und Nachweise

ORD-Eintrag
ord-6178727dfe674edf8d77ca2c1b17ae58
Quelldatensatz
uspto-grants-2006_11
Patentnummer
US07141567B2

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