Hydrochloric Acid → HCID 86639984, compound

HRID 1359921Notes

Reaction equation

HRID 1359921 reaction equation
[OH-].[Na+].[C:3]([C:5]1[CH:10]=[C:9]([C@:11]2([O:29][C@H:28]([CH2:30][O:31]C(=O)C)[C@@H:23]([O:24]C(=O)C)[C@H:18]([O:19]C(=O)C)[C@H:13]2[O:14]C(=O)C)[OH:12])[CH:8]=[C:7]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([CH2:42][CH3:43])=[CH:38][CH:37]=2)[C:6]=1[CH3:44])#[N:4].Cl>CO.C1COCC1>[C:3]([C:5]1[CH:10]=[C:9]([C@:11]2([O:29][C@H:28]([CH2:30][OH:31])[C@@H:23]([OH:24])[C@H:18]([OH:19])[C@H:13]2[OH:14])[OH:12])[CH:8]=[C:7]([CH2:35][C:36]2[CH:37]=[CH:38][C:39]([CH2:42][CH3:43])=[CH:40][CH:41]=2)[C:6]=1[CH3:44])#[N:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86639985HCID 86639985, compound

Product 1

HCID 86639984HCID 86639984, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1.7 mL, 4 mol/L) is added to 1-cyano-3-(4-ethylbenzyl)-2-methyl-5-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzene (0.85 g) dissolved in methanol (6 mL) and THF (3 mL). The solution is stirred at room temperature for 1 h and then neutralized with hydrochloric acid (1 mol/L). After removal of the organic solvents, the residue is diluted with aqueous sodium bicarbonate solution and the resulting mixture is extracted with ethyl acetate. The combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1).

Workup

  1. customAfter removal of the organic solvents
  2. additionthe residue is diluted with aqueous sodium bicarbonate solution
  3. extractionthe resulting mixture is extracted with ethyl acetate
  4. dry with materialThe combined organic extracts are dried (sodium sulphate)
  5. customthe solvent is evaporated
  6. customThe remainder is purified by chromatography on silica gel (dichloromethane/methanol 1:0->8:1)

Sources & evidence

ORD record
ord-017208b652c04e9ab9dd4794a5e30f24
Source dataset
uspto-grants-2011_02
Patent number
US07879806B2

Reaction notes

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