反应详情

Acetyl chloride (10.0 μL, 0.14 mmol) was added to a stirred solution of 4d (50.0 mg, 0.11 mmol) and triethylamine (38.0 μL, 0.27 mmol) in THB (900 μL) at room temperature. After approximately 18 h, the reaction mixture was poured into saturated aqueous sodium bicarbonate and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude intermediary acylhydrazide was treated with thionyl chloride (˜1 mL, excess), and the resulting mixture was aged for approximately 18 h. The reaction mixture was poured carefully into cold saturated aqueous sodium bicarbonate and extracted three times with methylene chloride. The combined organic extracts were washed with brine, dried (Na2SO4) and concentrated in vacuo. The crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 20-100% acetonitrile/water as eluent, 0.1% TFA as modifier). Lyophilization of the purified fractions afforded the title compound 5d, m/z (ES) 488 (MH)+.

1. extractionextracted three times with methylene chloride
2. washThe combined organic extracts were washed with brine
3. dry with materialdried (Na2SO4)
4. concentrationconcentrated in vacuo
5. additionThe crude intermediary acylhydrazide was treated with thionyl chloride (˜1 mL, excess)
6. waitthe resulting mixture was aged for approximately 18 h
7. additionThe reaction mixture was poured carefully into cold saturated aqueous sodium bicarbonate
8. extractionextracted three times with methylene chloride
9. washThe combined organic extracts were washed with brine
10. dry with materialdried (Na2SO4)
11. concentrationconcentrated in vacuo
12. customThe crude residue was purified by preparative reversed phase HPLC on YMC Pack Pro C18 stationary phase (gradient elution; 20-100% acetonitrile/water as eluent, 0.1% TFA as modifier)