Multi-step reaction with 10 steps
1: 98.2 percent / DMAP / 5 h / 70 °C
2: 94.3 percent / Cu(NO3)2*3H2O, Ac2O, AcOH / 1 h / 0 - 20 °C
3: 1 N NaOH / methanol
4: imidazole / dimethylformamide / 3 h / Ambient temperature
5: FeCl3*6H2O, C, NH2-NH2*H2O / methanol; H2O / 5 h / 70 °C
6: Et3N / CH2Cl2 / 1.5 h / 0 - 20 °C
7: 1.) NaH / 1.) DMF, 0 deg C, 30 min, 2.) DMF, RT, 2 h
8: NH2-NH2*H2O / ethanol / 1 h / Heating
9: WSCD*HCl, HOBt / dimethylformamide / 2 h / Ambient temperature
10: TBAF / tetrahydrofuran / 1 h / Ambient temperature
With
1H-imidazole; dmap; sodium hydroxide; WSCD*HCl; tetrabutyl ammonium fluoride; acetic anhydride; iron(III) chloride; sodium hydride; benzotriazol-1-ol; copper(II) nitrate; hydrazine hydrate; acetic acid; triethylamine;
In
tetrahydrofuran; methanol; ethanol; dichloromethane; water; N,N-dimethyl-formamide;
DOI:10.1021/jm980300f