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

HRID 985382Notes

Reaction equation

HRID 985382 reaction equation
[CH:1]([OH:4])([CH3:3])[CH3:2].Cl[C:6](Cl)([O:8]C(=O)OC(Cl)(Cl)Cl)Cl.[O:17]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[CH2:35][C:36]1[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=1)[C@@H:18]1[O:26][C@H:25]([CH2:27][OH:28])[C@@H:23]([OH:24])[C@H:21]([OH:22])[C@H:19]1[OH:20].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC1C=C(C)C=C(C)N=1>[CH:1]([O:4][C:6]([O:28][CH2:27][C@H:25]1[O:26][C@@H:18]([O:17][C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH2:35][C:36]2[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=2)[C@H:19]([OH:20])[C@@H:21]([OH:22])[C@@H:23]1[OH:24])=[O:8])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 3776IsopropanolHCID 94429TriphosgeneHCID 10177526Sergliflozin

Product 1

HCID 207687432-(4-methoxybenzyl)-phenyl 6-O-isopropyloxycarbonyl-beta-D-glucopyranosideYield 70%

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of isopropanol (0.12 g) in 2,4,6-trimethylpyridine (2 mL) was added triphosgene (0.022 g) at 0° C., and the mixture was stirred for 1 hour. Thereafter, 2-(4-methoxybenzyl)phenyl β-D-glucopyranoside (0.075 g) was added to the reaction mixture, and the mixture was stirred at room temperature overnight. 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 water, and dried over 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-isopropyloxycarbonyl-β-D-glucopyranoside (0.024 g).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 10% aqueous citric acid solution and water
  4. dry with materialdried over magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-2cec83ef664f44489c8f0c1b59559bc3
Source dataset
uspto-grants-2005_03
Patent number
US06872706B2

Reaction notes

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