Citric Acid → HCID 68442598, compound

HRID 1592826Notes

Reaction equation

HRID 1592826 reaction equation
[C@@H:1]1([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:16]([CH3:27])[N:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:14]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].CC1C=CC=C(C)N=1.Cl[C:43]([O:45][CH2:46][CH3:47])=[O:44].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[CH2:46]([O:45][C:43]([O:11][CH2:10][C@H:8]1[O:9][C@@H:1]([O:12][C:13]2[C:17]([CH2:18][C:19]3[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=3)=[C:16]([CH3:27])[N:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[N:14]=2)[C@H:2]([OH:3])[C@@H:4]([OH:5])[C@@H:6]1[OH:7])=[O:44])[CH3:47]

Participants

6

Reactant 4

HCID 311Citric AcidHCID 79372,6-LutidineHCID 10928Ethyl chloroformateHCID 68441022HCID 68441022, compound

Product 1

HCID 68442598HCID 68442598, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of 3-(β-D-glucopyranosyloxy)-4-[(4-methoxyphenyl)methyl]-5-methyl-1-phenyl-1H-pyrazole (0.18 g) and 2,6-dimethylpyridine (0.069 mL) in acetonitrile (5 mL) was added ethyl chloroformate (0.045 mL), 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 brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=15/1) to give the title compound (0.13 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=15/1)

Sources & evidence

ORD record
ord-96559213aa074240a030590651da4cb3
Source dataset
uspto-grants-2007_11
Patent number
US07294618B2

Reaction notes

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