反应详情

温度

-78 °C

An NH3 (10 mL) solution of 6-{3-[N,O-bis(phenoxycarbonyl)hydroxylamino]-1-butyn-1-yl}-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4-tetrahydroisoquinoline (310 mg, 0.47 mmol) in a sealed tube is stirred at ambient temperature for 12 hours. The mixture is then cooled to -78° C. and the reaction vessel carefully opened. The ammonia is allowed to evaporate and the resulting material is partitioned between EtOAc (60 mL) and H2O (10 mL). The aqueous phase is extracted with EtOAc (1×25 mL) and the combined organic phases are washed with saturated NaHCO3 solution (2×50 mL), saturated NaCl solution (2×5 mL), dried over MgSO4 and concentrated in vacuo- The resulting pale yellow solid is chromatographed (silica gel, EtOAc then 10% MeOH/CH2Cl2) to afford 6-[3-(N-aminocarbonyl-N-hydroxyamino)-1-butyn-1-yl]-2-{[5-(4-fluorophenyl)-2-pyridyl]-methyl}-1-oxo-1,2,3,4 -tetrahydroisoquinoline, m.p. 118°-120°C.

1. customto evaporate
2. customthe resulting material is partitioned between EtOAc (60 mL) and H2O (10 mL)
3. extractionThe aqueous phase is extracted with EtOAc (1×25 mL)
4. washthe combined organic phases are washed with saturated NaHCO3 solution (2×50 mL), saturated NaCl solution (2×5 mL)
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo- The resulting pale yellow solid
7. customis chromatographed (silica gel, EtOAc