Réaction #7480

Équation de réaction

sodium hydroxide

3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

cesium carbonate

2-bromoethyl acetate

→

3-(β-D-glucopyranosyloxy)-1-(2-hydroxyethyl)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole

Solvants

N,N-dimethylformamide

methanol

water

Conditions de réaction

Traitement

1. 1
   workup.DISTILLATIONthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)
2. 2
   AutreThe obtained crude product
3. 3
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
4. 4
   AutreThe solvent was removed under reduced pressure
5. 5
   Autrethe residue was purified by column chromatography on ODS (developing solvent: methanol/water=3/2)

Mode opératoire

To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (33 mg) and cesium carbonate (138 mg) in N,N-dimethylformamide (1 mL) was added 2-bromoethyl acetate (0.035 mL) at 40° C., and the mixture was stirred for 2 hours. To the reaction mixture was added water, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol). The obtained crude product was dissolved in methanol (1 mL), and to the solution was added 2 mol/L aqueous sodium hydroxide solution (0.04 mL), and the mixture was stirred at room temperature for 30 minutes. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on ODS (developing solvent: methanol/water=3/2) to give 3-(β-D-glucopyranosyloxy)-1-(2-hydroxyethyl)-5-methyl-4-[(4-cyclopropylphenyl)methyl]-1H-pyrazole (8 mg).

Source