Water → HCID 131728196, compound

HRID 502859Notes

Reaction equation

HRID 502859 reaction equation
[CH3:1][O:2][CH2:3][CH2:4]Br.[OH:6][C@:7]1([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([OH:33])=[CH:29][CH:28]=3)[CH:19]=2)[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9].C(=O)([O-])[O-].[Cs+].[Cs+].O>CN(C)C=O.[Cl-].[Na+].O>[OH:6][C@:7]1([C:18]2[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[C:20]([CH2:26][C:27]3[CH:28]=[CH:29][C:30]([O:33][CH2:4][CH2:3][O:2][CH3:1])=[CH:31][CH:32]=3)[CH:19]=2)[O:15][C@H:14]([CH2:16][OH:17])[C@@H:12]([OH:13])[C@H:10]([OH:11])[C@H:8]1[OH:9]

Participants

7

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 809722-Bromoethyl methyl etherHCID 866102154-(beta-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzonitrile

Product 1

HCID 131728196HCID 131728196, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

2-Bromoethyl methyl ether (85 μl) is added to a mixture of 4-(β-D-glucopyranos-1-yl)-2-(4-hydroxybenzyl)-benzonitrile (0.30 g) and cesium carbonate (0.39 g) in 3 mL of dimethylformamide. The mixture is stirred at 80° C. for 16 h, before water and brine are added. The resulting mixture is extracted with ethyl acetate, the combined extracts are dried over sodium sulphate and the solvent is removed under reduced pressure. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1).

Workup

  1. additionare added
  2. extractionThe resulting mixture is extracted with ethyl acetate
  3. dry with materialthe combined extracts are dried over sodium sulphate
  4. customthe solvent is removed under reduced pressure
  5. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0->5:1)

Sources & evidence

ORD record
ord-d3f8e0a1bc1749f8904d86c083e8d917
Source dataset
uspto-grants-2010_08
Patent number
US07776830B2

Reaction notes

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