Multi-step reaction with 9 steps
1.1: dichloromethane / 0.5 h / 0 - 20 °C / Inert atmosphere
2.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
2.2: 8 h / 0 - 20 °C / Inert atmosphere
3.1: lithium hydroxide / water; tetrahydrofuran; methanol / 1 h / 0 - 20 °C / Inert atmosphere
4.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
4.2: 8 h / 0 - 20 °C / Inert atmosphere
5.1: dichloromethane / 3 h / 0 - 20 °C / Inert atmosphere
6.1: N-ethyl-N,N-diisopropylamine; pentafluorophenyl diphenyl-phosphinate / acetonitrile / 24.5 h / -5 - 20 °C / Inert atmosphere
7.1: lithium hydroxide / water; tetrahydrofuran; methanol / 1 h / 0 - 20 °C / Inert atmosphere
8.1: benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride / dichloromethane / 0.25 h / 0 °C / Inert atmosphere
8.2: 8 h / 0 - 20 °C / Inert atmosphere
9.1: hydrogen; palladium on activated charcoal / methanol / 1 h / 760.05 Torr
With
palladium on activated charcoal; pentafluorophenyl diphenyl-phosphinate; hydrogen; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; lithium hydroxide;
In
tetrahydrofuran; methanol; dichloromethane; water; acetonitrile;
DOI:10.1021/ol5002126