تفاعل #318105
ord-3480a75802764e67a0d691650e0fb7f4
معادلة التفاعل
المتفاعلات
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المعالجة
- 1استخلاصthe resulting mixture was extracted with ethyl acetate
- 2غسيلThe extract was washed with water
- 3تجفيفa saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate
- 4أخرىThe solvent was removed under reduced pressure
- 5أخرىthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2)
الإجراء التجريبي
To a solution of 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-carboxyphenyl)ethyl]benzofuran (0.12 g) in N,N-diemthylformamide (2 mL) were added benzyl 2-aminoacetate hydrochloride (48 mg), 1-hydroxybenzotriazole (32 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (77 mg) and triethylamine (0.11 mL), and the mixture was stirred at room temperature for three days. The reaction mixture was poured into 1 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with water, a saturated aqueous sodium hydrogen carbonate solution and brine successively, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-{2-[4-(benzyloxycarbonylmethylcarbamoyl)phenyl]ethyl}benzofuran (94 mg). This material was dissolved in methanol (3 mL). To the solution was added 10% palladium-carbon powder (40 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 1 hour. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (82 mg).