Hydrochloric Acid → HCID 86664426, Verbindung

HRID 46192Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 46192
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[C@H:13]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C@@H:12]([O:22][CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[C@H:11]([O:30][CH2:31][C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]3[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=3)[O:9]2)=[CH:4][C:3]=1[CH:47]([C:52]1[N:53]=[N:54][C:55]([Cl:58])=[CH:56][CH:57]=1)C(OC)=O.CO.[OH-].[Li+].Cl>O1CCCC1.O>[Cl:58][C:55]1[N:54]=[N:53][C:52]([CH2:47][C:3]2[CH:4]=[C:5]([C@H:8]3[C@H:13]([O:14][CH2:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)[C@@H:12]([O:22][CH2:23][C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)[C@H:11]([O:30][CH2:31][C:32]4[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=4)[C@@H:10]([CH2:38][O:39][CH2:40][C:41]4[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=4)[O:9]3)[CH:6]=[CH:7][C:2]=2[Cl:1])=[CH:57][CH:56]=1

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 86664427HCID 86664427, Verbindung2×

Produkt 1

HCID 86664426HCID 86664426, VerbindungAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To a solution of Methyl 2-(2-chloro-5-((2S,3S,4R,5R,6R)-3,4,5-tris(benzyloxy)-6-(benzyloxymethyl)-tetrahydro-2H-pyran-2-yl)phenyl)-2-(6-chloropyridazin-3-yl)acetate (compound 23, 9.9 g, 12 mmol) from Step 1 in terahydrofuran (40 mL) was added methanol (56 mL) and lithium hydroxide solution (0.1 M in water, 180 mL, 180 mmol). The reaction mixture was allowed to stir at room temperature overnight. After cooling to 0° C., hydrochloric acid (1.0 M) was added to neutralize the reaction mixture. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The resulting residue was slurried in methanol (100 mL) and the slurry was stirred at ambient temperature for 2 h. The resulting solid was isolated by filtration and dried in vacuo to yield the title compound (7.8 g, 10 mmol, 86%) as a white solid.

Aufarbeitung

  1. temperatureAfter cooling to 0° C.
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. stirringthe slurry was stirred at ambient temperature for 2 h
  8. customThe resulting solid was isolated by filtration
  9. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-a809bb9576a44f1a8a4bb5645da53935
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08541380B2

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