Multi-step reaction with 14 steps
1.1: triethylamine; dmap / dichloromethane / Reflux
2.1: hydrogen bromide; acetic acid; acetic anhydride / toluene / 1.5 h / 105 °C
3.1: acetic acid; sodium acetate; sodium dichromate dihydrate; acetic anhydride / toluene / 60 °C
4.1: potassium hydroxide / toluene; ethanol / 1 h / 20 °C
5.1: pyridinium chlorochromate / dichloromethane / 1 h / 20 °C
6.1: triethylamine / 20 °C
7.1: Dess-Martin periodane / dichloromethane / 2 h / 20 °C
8.1: acetic acid; sodium nitrite / dimethyl sulfoxide / 0 - 20 °C
9.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 1 h / 0 - 20 °C
10.1: hydrogenchloride; water / 20 - 45 °C
11.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 1 h / 20 °C
12.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C
13.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; dmap / dichloromethane / 20 °C
14.1: dmap; 1H-tetrazole / dichloromethane / 2 h / 20 °C
14.2: 0.5 h / 0 °C
With
1H-tetrazole; hydrogenchloride; dmap; sodium dichromate dihydrate; water; hydrogen bromide; sodium acetate; acetic anhydride; Dess-Martin periodane; acetic acid; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; N-ethyl-N,N-diisopropylamine; HATU; pyridinium chlorochromate; trifluoroacetic acid; potassium hydroxide; sodium nitrite;
In
ethanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide; toluene;