Sodium Chloride → 1-chloro-2-(4-cyclopentyloxybenzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

HRID 2106421

Reaktionsgleichung

Reaktionsgleichung von HRID 2106421
I[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@:14]2([O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]([OH:19])[C@H:16]2[OH:17])[OH:15])=[CH:10][C:9]=1[CH2:26][C:27]1[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[Cl-].[Na+]>CN(C)C=O>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C@:14]2([O:23][C@H:22]([CH2:24][OH:25])[C@@H:20]([OH:21])[C@H:18]([OH:19])[C@H:16]2[OH:17])[OH:15])=[CH:10][C:9]=1[CH2:26][C:27]1[CH:28]=[CH:29][C:30]([O:33][CH:2]2[CH2:6][CH2:5][CH2:4][CH2:3]2)=[CH:31][CH:32]=1

Komponenten

6

Edukt 4

HCID 5234Sodium ChlorideHCID 10796Cesium carbonate2×HCID 73784Iodocyclopentane2×HCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Produkt 1

HCID 866006791-chloro-2-(4-cyclopentyloxybenzyl)-4-(beta-D-glucopyranos-1-yl)-benzene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

0.16 ml iodocyclopentane are added to a mixture of 0.25 g 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.4 g caesium carbonate in 2.5 ml of dimethylformamide. The mixture is stirred for 4 h at 45° C., before another 0.1 g caesium carbonate and 0.05 ml iodocyclopentane are added. After another 14 h stirring at 45° C. aqueous sodium chloride solution is added and the mixture is extracted with ethyl acetate. The organic phase is dried over sodium sulphate, the solvent is removed and the residue is purified using silica gel (dichloromethane/methanol 1:0->5:1).

Aufarbeitung

  1. additionare added
  2. additionis added
  3. extractionthe mixture is extracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulphate
  5. customthe solvent is removed
  6. customthe residue is purified

Quellen und Nachweise

ORD-Eintrag
ord-997cbc210cf7492eb16dba9614771870
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07579449B2

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