Multi-step reaction with 7 steps
1: acetic anhydride / 3 h / Reflux
2: hydroquinidine (anthraquinone-1,4-diyl) diether / methanol; diethyl ether; tetrahydrofuran / 24 h / -40 °C / Inert atmosphere
3: diphenyl phosphoryl azide; triethylamine / toluene / 1 h / 100 °C
4: sodium hydroxide / methanol; water / 12 h / 20 °C / Cooling with ice
5: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 96 h / 20 °C
6: 10 wt% Pd(OH)2 on carbon; hydrogen / methanol / 16 h / 20 °C
7: N-ethyl-N,N-diisopropylamine; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate / 1,2-dichloro-ethane / 2 h / 20 °C
With
diphenyl phosphoryl azide; 10 wt% Pd(OH)2 on carbon; hydrogen; acetic anhydride; benzotriazol-1-ol; N,N,N',N'-tetramethylchloroformamidinium hexafluorophosphate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; sodium hydroxide; hydroquinidine (anthraquinone-1,4-diyl) diether;
In
tetrahydrofuran; methanol; diethyl ether; water; 1,2-dichloro-ethane; N,N-dimethyl-formamide; toluene;
DOI:10.1016/j.bmc.2018.04.051