Water → HCID 86611026, compound

HRID 2245915Notes

Reaction equation

HRID 2245915 reaction equation
[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]([OH:27])=[CH:23][CH:22]=1.C1(C)C=CC(S([O:37][CH:38]2[CH2:42][CH2:41][CH:40](O)[CH2:39]2)(=O)=O)=CC=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O>[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][CH:40]2[CH2:41][CH2:42][CH:38]([OH:37])[CH2:39]2)=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 58597012HCID 58597012, compoundHCID 866006741-Chloro-4-(beta-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene

Product 1

HCID 86611026HCID 86611026, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 1-chloro-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene (0.25 g), 3-hydroxy-cyclopent-1-yl p-tolylsulfonate (0.19 g) and cesium carbonate (0.33 g) in dimethylformamide (1.5 mL) is stirred at 70° C. for 16 h. After cooling to ambient temperature, water is added and the resultant mixture is 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).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. dry with materialThe combined organic phases are dried (Na2SO4)
  4. customthe solvent is removed
  5. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→4:1)

Sources & evidence

ORD record
ord-661143650a344a7e81672257f4ce2257
Source dataset
uspto-grants-2010_03
Patent number
US07683160B2

Reaction notes

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