Multi-step reaction with 14 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: O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; N-ethyl-N,N-diisopropylamine / dichloromethane; N,N-dimethyl-formamide / 14 h / 20 °C
6: hydrogenchloride / 1,4-dioxane / 2 h / 20 °C
7: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / N,N-dimethyl-formamide / 17 h / 20 °C
8: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 22 h / 20 °C
9: pyridine; pyridine hydrogenfluoride / tetrahydrofuran / 12 h / 40 °C
10: dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 6 h / 0 - 20 °C
11: ammonium acetate; zinc / tetrahydrofuran; water / 22.5 h / 20 °C
12: diethylamine / acetonitrile / 4 h / 20 °C
13: 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 23 h / 20 °C
14: 2,6-dimethylpyridine; water; silver nitrate / tetrahydrofuran / 1.5 h / 65 °C
With
pyridine; 2,6-dimethylpyridine; hydrogenchloride; dmap; 1-hydroxy-7-aza-benzotriazole; ammonium acetate; 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; water; N,N-dimethyl-formamide; acetonitrile;
DOI:10.1016/j.tet.2011.10.094