Reacción #7486

ord-9a0224bc18ff4dde8591bc36f4b1149a

Ecuación de reacción

O
water
CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1
3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
OCCCBr
3-bromopropanol
→
CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)nn(CCCO)c2C)cc1
3-(β-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole

Reactantes

O
water
CSc1ccc(Cc2c(O[C@@H]3O[C@H](CO)[C@@H](O)[C@H](O)[C@H]3O)n[nH]c2C)cc1
3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole
O=C([O-])[O-].[Cs+].[Cs+]
cesium carbonate
OCCCBr
3-bromopropanol

Reactivos

Ninguno

Disolventes

CN(C)C=O
N,N-dimethylformamide

Condiciones de reacción

Temperatura
40°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    workup.DISTILLATIONthe mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Procedimiento

To a suspension of 3-(β-D-glucopyranosyloxy)-5-methyl-4-[(4-methylthiophenyl)methyl]-1H-pyrazole (0.020 g) and cesium carbonate (0.11 g) in N,N-dimethylformamide (0.5 mL) was added 3-bromopropanol (0.022 mL), and the mixture was stirred at 40° C. overnight. To the reaction mixture was added water, and the mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol), and successively by column chromatography on silica gel (eluent: dichloromethane/methanol=5/1) to give 3-(β-D-glucopyranosyloxy)-1-(3-hydroxypropyl)-5-methyl-4-[(4methylthiophenyl)methyl]-1H-pyrazole (0.011 g).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07087579B2uspto-grants-2006_08