Multi-step reaction with 13 steps
1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane; N,N-dimethyl-formamide / 6 h / 20 °C
2: hydrogenchloride / 1,4-dioxane / 1 h / 10 - 15 °C
3: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 12 h / 20 °C
4: hydrogenchloride / 1,4-dioxane / 1 h / 0 °C
5: benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 22 h
6: hydrogenchloride / 1,4-dioxane
7: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / dichloromethane; N,N-dimethyl-formamide / 25 h
8: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 12 h
9: pyridine hydrogenfluoride
10: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 4 h / 0 - 20 °C
11: water; silver nitrate; zinc / tetrahydrofuran
12: diethylamine / acetonitrile
13: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 40 h / 0 - 20 °C
With
hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; water; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; pyridine hydrogenfluoride; silver nitrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; diethylamine; triethylamine; N-ethyl-N,N-diisopropylamine; zinc;
In
tetrahydrofuran; 1,4-dioxane; dichloromethane; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.10.094