Hydrochloric Acid → HCID 9847831, compound

HRID 1982861Notes

Reaction equation

HRID 1982861 reaction equation
[O:1]([C:13]1[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=1[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([CH2:28][CH3:29])=[CH:24][CH:23]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].Cl[C:31]([O:33][CH2:34][CH3:35])=[O:32].Cl>CC1C=C(C)C=C(C)N=1>[CH2:34]([O:33][C:31]([O:12][CH2:11][C@H:9]1[O:10][C@@H:2]([O:1][C:13]2[CH:18]=[C:17]([CH2:19][OH:20])[CH:16]=[CH:15][C:14]=2[CH2:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][CH3:29])=[CH:26][CH:27]=2)[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])=[O:32])[CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 10928Ethyl chloroformateHCID 9822503HCID 9822503, compound

Product 1

HCID 9847831HCID 9847831, compoundYield 22.6%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 2-(4-ethylbenzyl)-5-hydroxymethylphenyl β-D-glucopyranoside (0.075 g) in 2,4,6-trimethypyridine (2 mL) was added ethyl chloroformate (0.037 mL, 2 mol equivalent), and the mixture was stirred at room temperature for 17 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, and the mixture was extracted with ethyl acetate. The extract was washed with 1 mol/L hydrochloric acid and water, and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/-methanol=10/1) and recrystallized (recrystallization solvent: acetone/hexane=1/1) to give 2-(4-ethylbenzyl)-5-hydroxymethylphenyl 6-O-ethoxycarbonyl-β-D-glucopyranoside (0.020 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with 1 mol/L hydrochloric acid and water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/-methanol=10/1)
  6. customrecrystallized
  7. custom(recrystallization solvent: acetone/hexane=1/1)

Sources & evidence

ORD record
ord-73d15e4ad51b46e0bd92fda0bb94d1df
Source dataset
uspto-grants-2009_06
Patent number
US07541341B2

Reaction notes

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