Citric Acid → 2-(4-methoxybenzyl)phenyl 6-O-hexanoyl-beta-D-glucopyranoside

HRID 985381Notes

Reaction equation

HRID 985381 reaction equation
[O:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=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].[C:28](Cl)(=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC1C=C(C)C=C(C)N=1>[C:28]([O:12][CH2:11][C@H:9]1[O:10][C@@H:2]([O:1][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])(=[O:34])[CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 67340Hexanoyl chlorideHCID 10177526Sergliflozin

Product 1

HCID 690157792-(4-methoxybenzyl)phenyl 6-O-hexanoyl-beta-D-glucopyranosideYield 23.8%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 2-(4-methoxybenzyl)phenyl β-D-glucopyranoside (0.10 g) in 2,4,6-trimethylpyridine (2 mL) was added hexanoyl chloride (0.072 g) at 0° C., and the mixture was stirred for 3 hours. To the reaction mixture was added 10% aqueous citric acid solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with 10% aqueous citric acid solution and brine. The organic layer was 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) to give 2-(4-methoxybenzyl)phenyl 6-O-hexanoyl-β-D-glucopyranoside (0.030 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with 10% aqueous citric acid solution and brine
  3. dry with materialThe organic layer was dried 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)

Sources & evidence

ORD record
ord-8e75ab55c54f4e96b3698894c0dcf063
Source dataset
uspto-grants-2005_03
Patent number
US06872706B2

Reaction notes

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