Hydrochloric Acid → HCID 57802392, compound

HRID 1365030Notes

Reaction equation

[CH2:1]([C:8]1[C:9]([O:23][C@@H:24]2[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]2[OH:26])=[N:10][N:11]([CH:20]([CH3:22])[CH3:21])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:41](Br)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1.Cl>CN(C)C=O>[CH2:1]([C:8]1[C:9]([O:23][C@@H:24]2[O:32][C@H:31]([CH2:33][OH:34])[C@@H:29]([OH:30])[C@H:27]([OH:28])[C@H:25]2[OH:26])=[N:10][N:11]([CH:20]([CH3:22])[CH3:21])[C:12]=1[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH2:41][C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a suspension of 4-benzyl-3-(β-D-glucopyranosyloxy)-5-(4-hydroxyphenyl)-1-isopropyl-1H-pyrazole (0.02 g) and potassium carbonate (0.017 g) in N,N-dimethylformamide (20 mL) was added benzyl bromide at room temperature. The reaction mixture was stirred at 50° C. for 3 hours. After the reaction mixture was acidified by adding a hydrochloric acid aqueous solution (1 mol/L), the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure and the residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=5/1) to give the title compound.

Workup

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

Sources & evidence

ORD record: ord-a542aefd3c704204a42f981ec461e007
Source dataset: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07888487B2

Reaction notes

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