反应详情

A solution of N-(1-(4-chlorobenzyl)-3-pent-4-enoylcyclobutyl)formamide (0.5 g, 1.64 mmol) and ammonium acetate (1.14 g, 9.84 mmol) in 2,2,2-trifluoroethanol (4 mL). was treated with tert-butyl isocyanide (1.1 mL, 9.84 mmol) and stirred at room temperature for 3 days. Once complete, the solution was diluted with ethyl acetate (15 mL) and quenched with 2M HCl (10 mL). After stirring vigorously for 1 h, the phases were separated and the organic layer was washed with water and saturated aqueous sodium chloride, dried over MgSO4, filtered and concentrated. Purification by column chromatography (gradient 25-75% ethyl acetate in heptane) afforded the subject compound as a colorless oil (330, mg, 45% yield). ESI MS found for C24H34ClN3O3 m/z [448.6 (M+1), 470.6 (M+Na+), 446.3 (M−1)].

1. customquenched with 2M HCl (10 mL)
2. stirringAfter stirring vigorously for 1 h
3. customthe phases were separated
4. washthe organic layer was washed with water and saturated aqueous sodium chloride
5. dry with materialdried over MgSO4
6. filtrationfiltered
7. concentrationconcentrated
8. customPurification by column chromatography (gradient 25-75% ethyl acetate in heptane)