Multi-step reaction with 11 steps
1.1: acetic acid / water / 22.5 h / 20 - 70 °C
2.1: sulfuric acid / dichloromethane / 0 - 20 °C
2.2: pH 9 / Cooling with ice
3.1: palladium 10% on activated carbon; hydrogen; acetic acid / ethanol / 20 °C / 1551.49 Torr
3.2: pH 9
4.1: hydrogenchloride; water / 24 h / Reflux
5.1: triethylamine / 1,4-dioxane; water / 6 h / 20 °C
6.1: 4-methyl-morpholine; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C
7.1: hydrogenchloride / 1,4-dioxane / 3 h / 20 °C
8.1: triethylamine / 1,4-dioxane
8.2: -78 - 20 °C
9.1: lithium hydroxide / tetrahydrofuran; water / 3 h
10.1: 4-methyl-morpholine; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane; N,N-dimethyl-formamide / 0 - 20 °C
11.1: dichloro-acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / toluene / 0 - 20 °C
With
4-methyl-morpholine; hydrogenchloride; dichloro-acetic acid; sulfuric acid; palladium 10% on activated carbon; water; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; acetic acid; dimethyl sulfoxide; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; lithium hydroxide;
In
tetrahydrofuran; 1,4-dioxane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene;
DOI:10.1002/jlcr.1905