Hydrochloric Acid → HCID 86656437, compound

HRID 1038353Notes

Reaction equation

HRID 1038353 reaction equation
[OH-].[Na+].[CH2:3]([C:5]1[CH:45]=[CH:44][C:8]([CH2:9][C:10]2[C:15]([C:16]#[N:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([C@:20]3([O:38][C@H:37]([CH2:39][O:40]C(=O)C)[C@@H:32]([O:33]C(=O)C)[C@H:27]([O:28]C(=O)C)[C@H:22]3[O:23]C(=O)C)[OH:21])[CH:11]=2)=[CH:7][CH:6]=1)[CH3:4].Cl>CO.C1COCC1>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([CH2:9][C:10]2[C:15]([C:16]#[N:17])=[C:14]([O:18][CH3:19])[CH:13]=[C:12]([C@:20]3([O:38][C@H:37]([CH2:39][OH:40])[C@@H:32]([OH:33])[C@H:27]([OH:28])[C@H:22]3[OH:23])[OH:21])[CH:11]=2)=[CH:44][CH:45]=1)[CH3:4]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 86639987HCID 86639987, compound

Product 1

HCID 86656437HCID 86656437, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Aqueous sodium hydroxide solution (1.4 mL, 1 mol/L) is added to 6-(4-ethylbenzyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-2-methoxy-benzonitrile (0.16 g) dissolved in methanol (1 mL) and THF (1 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-fbf5295d984d42e3907461f94c3833c3
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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