Hydrochloric Acid → 1-Chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-(thiophen-3-yl-ethynyl)-benzyl]-benzene

HRID 502104

Reaction equation

HRID 502104 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:10]2[O:11]C(=O)C)[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]2[CH:45]=[CH:44][S:43][CH:42]=2)=[CH:35][CH:34]=1.[OH-].[K+].Cl>CO>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@:8]2([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:10]2[OH:11])[OH:9])=[CH:4][C:3]=1[CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:39]#[C:40][C:41]2[CH:45]=[CH:44][S:43][CH:42]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 866072521-Chloro-4-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranos-1-yl)-2-[4-(thiophen-3-yl-ethynyl)-benzyl]-benzene

Product 1

HCID 866072551-Chloro-4-(beta-D-glucopyranos-1-yl)-2-[4-(thiophen-3-yl-ethynyl)-benzyl]-benzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 0.52 g 1-chloro-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-[4-(thiophen-3-yl-ethynyl)-benzyl]-benzene in 9 mL methanol is added 0.85 mL of 4 M potassium hydroxide solution. The solution is stirred at ambient temperature for one hour and then neutralised with 1 M hydrochloric acid. After the methanol is evaporated the residue is combined with brine and the resultant mixture is extracted with ethyl acetate. The organic extracts are dried over sodium sulfate, and the solvent is removed. The residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→5:1).

Workup

  1. customAfter the methanol is evaporated the residue
  2. extractionthe resultant mixture is extracted with ethyl acetate
  3. dry with materialThe organic extracts are dried over sodium sulfate
  4. customthe solvent is removed
  5. customThe residue is purified by chromatography on silica gel (dichloromethane/methanol 1:0→5:1)

Sources & evidence

ORD record
ord-bf68c197e40f42478f62635132e39fba
Source dataset
uspto-grants-2010_08
Patent number
US07772378B2

Linked notes

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