Multi-step reaction with 10 steps
1: hydrogen; palladium on activated charcoal / methanol / 2 h / 20 °C
2: dicyclohexyl-carbodiimide; benzotriazol-1-ol / N,N-dimethyl-formamide / 15 h / 20 °C
3: 1,1,1,3,3,3-hexamethyl-disilazane; pyridine / 0.5 h / 20 °C
4: acetic acid / methanol / 11 h / 20 °C
5: methanesulfonyl chloride; triethylamine / chloroform / 0.5 h / 20 °C
6: potassium carbonate / N,N-dimethyl-formamide / 6 h / 100 °C
7: hydrogenchloride / methanol; water / 0.33 h / 20 °C
8: sodium hydroxide / methanol / 168 h / 20 °C
9: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 22 h / 20 °C
10: trifluoroacetic acid / 0.67 h / 0 °C
With
pyridine; hydrogenchloride; palladium on activated charcoal; hydrogen; potassium carbonate; benzotriazol-1-ol; acetic acid; methanesulfonyl chloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; dicyclohexyl-carbodiimide; 1,1,1,3,3,3-hexamethyl-disilazane; trifluoroacetic acid; sodium hydroxide;
In
methanol; chloroform; water; N,N-dimethyl-formamide;
DOI:10.1038/ja.2017.54