反应详情

To a solution of freshly prepared aluminum azide (0.6 mmol in 6 mL dry tetrahydrofuran) was added 120 mg benzyl-{2-[2-(3,5-dimethylphenyl)-5-isocyanato-1H-indol-3-yl]ethyl}-(4-pyridin-3-yl-butyl)amine and the mixture heated to reflux on an oil bath. After 20 hours, the mixture was cooled to room temperature concentrated poured into a mixture of 1M sodium potassium tartarate and ice, stirred vigorously for 40 minutes then partitioned between ethyl acetate and water. The organic portion was washed successively with 1M sodium potassium tartarate, water and brine then dried over sodium sulfate. Purification of the concentrate by flash chromatography on silica gel (methylene chloride:methanol, 88:12) gave the title compound (58 mg).

1. temperaturethe mixture heated
2. temperatureto reflux on an oil bath
3. concentrationconcentrated
4. additionpoured into a mixture of 1M sodium potassium tartarate and ice
5. customthen partitioned between ethyl acetate and water
6. washThe organic portion was washed successively with 1M sodium potassium tartarate, water and brine
7. dry with materialthen dried over sodium sulfate
8. customPurification of the
9. concentrationconcentrate by flash chromatography on silica gel (methylene chloride:methanol, 88:12)