Multi-step reaction with 9 steps
1: dmap; diisopropyl-carbodiimide / dichloromethane; water / 30 h / 0 °C / Inert atmosphere
2: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 20 °C / Inert atmosphere
3: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 5 h / 0 - 20 °C / Inert atmosphere
4: palladium 10% on activated carbon; hydrogen / ethanol / 3 h / 20 °C / Inert atmosphere
5: hydrogenchloride / 1,4-dioxane; water / 1 h / 20 °C
6: 1-hydroxy-7-aza-benzotriazole; N-ethyl-N,N-diisopropylamine; HATU / dichloromethane / 72 h / 0 - 20 °C / Inert atmosphere
7: trimethylamine hydrochloride; triethylamine / dichloromethane / 3 h / 20 °C / Inert atmosphere
8: sodium azide / N,N-dimethyl-formamide / 4 h / 50 °C / Inert atmosphere
9: copper(ll) sulfate pentahydrate; sodium L-ascorbate / water; tert-butyl alcohol / 10 h / 50 °C
With
hydrogenchloride; dmap; sodium azide; 1-hydroxy-7-aza-benzotriazole; copper(ll) sulfate pentahydrate; palladium 10% on activated carbon; hydrogen; trimethylamine hydrochloride; benzotriazol-1-ol; sodium L-ascorbate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; diisopropyl-carbodiimide;
In
1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; tert-butyl alcohol;
DOI:10.1016/j.bmcl.2011.10.045