반응 #61409

반응 방정식

water

citric acid monohydrate

1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazole

ethyl chloroformate

→

1-(benzyloxy-carbonyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole

용매

2,4,6-trimethylpyridine

반응 조건

후처리

1. 1
   추출the resulting mixture was extracted with ethyl acetate
2. 2
   세척The organic layer was washed with water
3. 3
   건조dried over anhydrous magnesium sulfate
4. 4
   기타the solvent was removed under reduced pressure
5. 5
   기타The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

실험 절차

To a solution of 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazole (0.20 g) in 2,4,6-trimethylpyridine (4 mL) was added ethyl chloroformate (0.092 mL), and the mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and citric acid monohydrate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, 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=10/1) to give 1-(benzyloxy-carbonyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (0.17 g).

출처