Pyridinium hydrochloride → HCID 86656438, compound

HRID 1038354Notes

Reaction equation

HRID 1038354 reaction equation
[CH2:1]([C:3]1[CH:43]=[CH:42][C:6]([CH2:7][C:8]2[CH:15]=[C:14]([C@:16]3([O:34][C@H:33]([CH2:35][O:36]C(=O)C)[C@@H:28]([O:29]C(=O)C)[C@H:23]([O:24]C(=O)C)[C@H:18]3[O:19]C(=O)C)[OH:17])[C:13]([O:40]C)=[CH:12][C:9]=2[C:10]#[N:11])=[CH:5][CH:4]=1)[CH3:2].Cl.[NH+]1C=CC=CC=1>O>[CH2:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:7][C:8]2[CH:15]=[C:14]([C@:16]3([O:34][C@H:33]([CH2:35][OH:36])[C@@H:28]([OH:29])[C@H:23]([OH:24])[C@H:18]3[OH:19])[OH:17])[C:13]([OH:40])=[CH:12][C:9]=2[C:10]#[N:11])=[CH:42][CH:43]=1)[CH3:2]

Participants

4

Reactant 2

HCID 21584435Pyridinium hydrochlorideHCID 86656439HCID 86656439, compound

Product 1

HCID 86656438HCID 86656438, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
215 °C

Procedure

A mixture of 2-(4-ethylbenzyl)-5-methoxy-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranos-1-yl)-benzonitrile (0.80 g) and pyridinium hydrochloride (9.0 g) is heated at 215° C. for 1 h. After cooling to ambient temperature, water is added and the resulting solution is extracted with ethyl acetate. The combined organic extracts are dried (MgSO4) and the solvent is removed under reduced pressure. The residue is dissolved in methanol (10 mL) and treated with 4 M aqueous NaOH solution (2.2 mL). The solution is stirred at room temperature for 1 h and then acidified using hydrochloric acid (4 mol/L). After removal of the organic solvents, the residue is extracted with ethyl acetate, the combined organic extracts are dried (sodium sulphate) and the solvent is evaporated. The remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water).

Workup

  1. temperatureAfter cooling to ambient temperature
  2. extractionthe resulting solution is extracted with ethyl acetate
  3. dry with materialThe combined organic extracts are dried (MgSO4)
  4. customthe solvent is removed under reduced pressure
  5. dissolutionThe residue is dissolved in methanol (10 mL)
  6. additiontreated with 4 M aqueous NaOH solution (2.2 mL)
  7. customAfter removal of the organic solvents
  8. extractionthe residue is extracted with ethyl acetate
  9. dry with materialthe combined organic extracts are dried (sodium sulphate)
  10. customthe solvent is evaporated
  11. customThe remainder is purified by HPLC on reversed phase (YMC C18, acetonitrile/water)

Sources & evidence

ORD record
ord-daa4817295aa40f7ba192dfe4e3ae06f
Source dataset
uspto-grants-2013_10
Patent number
US08551957B2

Reaction notes

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