反应详情

Compound 13a (115 mg, 0.29 mmol) was dissolved in 10 mL of anhydrous ethanol and hydrazine monohydrate (73 mg, 0.07 mL, 1.46 mmol) was added to the solution. The reaction mixture was heated to reflux overnight. Hydrazine monohydrate (0.07 mL) was added again and heating was continued overnight. The resulting solution was evaporated to dryness. The crude product was purified by column chromatography (4:1:0.5 chloroform:methanol:NH4OH). The desired fractions were collected, concentrated, and dried in vacuo to yield a sticky solid. The product was dissolved in 8 mL of EtOH and 2N H2SO4 was added drop wise. The salt that was precipitated out was filtered and washed with EtOH. This salt, which was hygroscopic in nature, was dissolved in water (2 mL) and lyophilized to give a white solid: yield 71 mg (65%), MS: m/z 381 (M+H)+; 1HNMR (D2O) δ 8.44 (s, 1H, H-2), 6.09 (d, 1H, H-1′, J1′,2′=5.6 Hz), 5.10 (dd, 1H, H-2′, J2′,3′=4.5 Hz), 4.53-4.62 (bm, 2H, H-3′, H-4′), 3.86-3.94 (m, 1H, 5′-CH2), 3.52-3.66 (m, 3H, 5′-CH2, N(CH3)—CH2), 2.95 (s, 3H, N—CH3), 2.86 (t, 2H, NHCO—CH2), 2.70 (s, 3H, 8-CH3); UV λmax, nm, pH 1, 258.4 (∈ 15,000), pH 7, 259.3 (∈ 15,200), pH 13, 260.4 (∈ 15,700). Anal. (C15H24N8O4.2.0H2SO4.2.7H2O) C, H, N, S.

1. temperatureThe reaction mixture was heated
2. temperatureto reflux overnight
3. temperatureheating
4. customThe resulting solution was evaporated to dryness
5. customThe crude product was purified by column chromatography (4:1:0.5 chloroform:methanol:NH4OH)
6. customThe desired fractions were collected
7. concentrationconcentrated
8. customdried in vacuo
9. customto yield a sticky solid
10. customThe salt that was precipitated out
11. filtrationwas filtered
12. washwashed with EtOH
13. dissolutionwas dissolved in water (2 mL)
14. customto give a white solid