Hydrochloric Acid → HCID 86611028, Verbindung

HRID 2245917Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2245917
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24]([O:27][C:28]2([C:33]([O:35]C)=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:23][CH:22]=1.Cl>[OH-].[K+].CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:17][C@H:16]([CH2:18][OH:19])[C@@H:14]([OH:15])[C@H:12]([OH:13])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:20][C:21]1[CH:22]=[CH:23][C:24]([O:27][C:28]2([C:33]([OH:35])=[O:34])[CH2:32][CH2:31][CH2:30][CH2:29]2)=[CH:25][CH:26]=1

Komponenten

5

Edukt 2

HCID 313Hydrochloric AcidHCID 86611027HCID 86611027, Verbindung

Produkt 1

HCID 86611028HCID 86611028, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 14797Potassium HydroxideLösungsmittel

Versuchsvorschrift

A solution of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-[4-(1-methoxycarbonyl-cyclopent-1-yloxy)-benzyl]-benzene (0.20 g) in aqueous potassium hydroxide solution (4 mol/l, 5 mL) and methanol (5 mL) is stirred at ambient temperature for 4 h. After neutralizing with aqueous hydrochloric acid (1 mol/l), the mixture is concentrated under reduced pressure, diluted with aqueous NaHCO3 solution and extracted with ethyl acetate. The combined organic phases are dried (Na2SO4), the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1).

Aufarbeitung

  1. concentrationthe mixture is concentrated under reduced pressure
  2. additiondiluted with aqueous NaHCO3 solution
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried (Na2SO4)
  5. customthe solvent is removed
  6. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Quellen und Nachweise

ORD-Eintrag
ord-44100a696ad041a68304f0e21641b32b
Quelldatensatz
uspto-grants-2010_03
Patentnummer
US07683160B2

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