反应详情

To a stirred solution of pent-4-en-1-ol (0.62 g, 7.21 mmol) and DIPEA (1.26 mL, 7.21 mmol) in anhydrous 1,4-dioxane (20 ml), at 10° C. and under nitrogen, was slowly added a solution of triphosgene (0.75 g, 2.52 mmol) in anhydrous 1,4-dioxane (20 mL). The reaction mixture was stirred at RT for 1 hour, and ethyl (2S)-2-aminonon-8-enoate*HCl (0.85 g, 3.61 mmol) and 1 M aqueous NaOH (7.21 ml, 7.21 mmol) added, and the reaction mixture was heated to 50° C. for 15 hours. After cooling to RT, the reaction mixture was basified to pH 8 with 1M aqueous NaOH and extracted with ether (3×200 ml). The combined organic phases were washed with water (100 mL), brine (50 mL), dried over Na2SO4, filtered and concentrated. The residue was chromatographed on silica gel (5 to 75% EtOAc in hexane) to give the title compound (0.96 g). LRMS (ESI) m/z 312.5 [(M+H)+; calcd for C17H30NO4: 312.2].

1. temperaturethe reaction mixture was heated to 50° C. for 15 hours
2. temperatureAfter cooling to RT
3. extractionextracted with ether (3×200 ml)
4. washThe combined organic phases were washed with water (100 mL), brine (50 mL)
5. dry with materialdried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was chromatographed on silica gel (5 to 75% EtOAc in hexane)