Cesium carbonate → HCID 86605979, compound

HRID 2246494Notes

Reaction equation

HRID 2246494 reaction equation
I[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[CH3:7][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+]>CN(C)C=O.[Cl-].[Na+].O>[CH3:7][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

Participants

6

Reactant 3

HCID 10796Cesium carbonate2×HCID 73784Iodocyclopentane2×HCID 86605980HCID 86605980, compound

Product 1

HCID 86605979HCID 86605979, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

0.17 mL iodocyclopentane are added to a mixture of 0.38 g 1-methyl-4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzene and 0.53 g cesium carbonate in 4 mL dimethylformamide. The mixture is stirred at 65° C. for 4 h, before another 0.35 g cesium carbonate and 0.1 mL iodocyclopentane are added. After stirring the mixture for an additional 14 h at 45° C. brine is added and the resulting mixture is extracted with ethyl acetate. The combined organic phases are dried over sodium sulfate, the solvent is removed and the residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1).

Workup

  1. additionare added
  2. additionis added
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic phases are dried over sodium sulfate
  5. customthe solvent is removed
  6. customthe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Sources & evidence

ORD record
ord-e86e86529ac5432682adfa28ce034c9f
Source dataset
uspto-grants-2010_03
Patent number
US07687469B2

Reaction notes

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