反应详情

To a solution of 1-(2-naphthylmethyl)-1H-imidazol-5-ylacetic acid hydrochloride (prepared in Example 4, 0.819 mg, 2.70 mmol) in dimethylformamide (15 ml) was added sequentially N, O-dimethylhydroxylamine hydrochloride (293 mg, 3.0 mmol), 3-hydroxy-1,2,3-benzotriazin-4(3H)-one (HOOBT, 489 mg, 3.0 mmol), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (EDC, 575 mg, 3.0 mmol) and triethylamine (1.67 ml, 12.0 mmol) and the resulting mixture stirred at room temperature for 18 h. Saturated aq. sodium bicarbonate (30 ml) and water (30 ml) were added and the mixture was extracted with methylene chloride (2×50 ml). The combined organic extracts were washed with brine (50 ml) and the solvent evaporated in vacuo. The residue was purified by flash chromatography (2-4% methanol/methylene chloride gradient elution) to provide the title compound as an oil.

1. extractionthe mixture was extracted with methylene chloride (2×50 ml)
2. washThe combined organic extracts were washed with brine (50 ml)
3. customthe solvent evaporated in vacuo
4. customThe residue was purified by flash chromatography (2-4% methanol/methylene chloride gradient elution)