Multi-step reaction with 11 steps
1: 32.48 g / triethylamine / methanol / 0.33 h
2: 98 percent / triethylamine / CH2Cl2 / 0.25 h / -30 °C
3: 1) sodium hydride / 1) DMF, room temperature, 1 h, 2) 60 deg C, 30 min
4: 68 percent / LiBH4 / tetrahydrofuran / 0.5 h / 60 °C
5: 87.4 percent / triethylamine / CH2Cl2 / 0.33 h / -30 °C
6: 78.1 percent / dimethylformamide / 1 h / 100 °C
7: 78 percent / H2NNH2*H2O / CH2Cl2; methanol / 5 h / 60 °C
8: 82 percent / triethylamine / CH2Cl2 / 0.33 h / -30 °C
9: 77 percent / NH3OH / methanol; H2O / 72 h / Ambient temperature
10: 1) AgNO3, pyridine, 2) H2S / 1) MeOH, CH2Cl2, H2O, room temperature, 10 min
11: diisopropylethylamine / acetonitrile / 4.5 h
With
pyridine; lithium borohydride; hydrogen sulfide; sodium hydride; hydrazine hydrate; silver nitrate; triethylamine; N-ethyl-N,N-diisopropylamine;
In
tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.7164/antibiotics.49.199