反応 #6753

反応方程式

water

citric acid monohydrate

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

ethyl chloroformate

→

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

溶媒

2,4,6-trimethylpyridine

反応条件

後処理

1. 1
   抽出the resulting mixture was extracted with ethyl acetate
2. 2
   洗浄The organic layer was washed with water
3. 3
   乾燥dried over anhydrous magnesium sulfate
4. 4
   その他the solvent was removed under reduced pressure
5. 5
   その他The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1)

実験手順

To a solution of 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (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-(benzyloxycarbonyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (0.17 g).

出典