Multi-step reaction with 8 steps
1.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 5 h / 2250.23 Torr
2.1: benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 16 h
3.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 6 h / 20 °C / 2250.23 Torr / Enzymatic reaction
4.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.17 h
4.2: 0.5 h
5.1: sodium hydroxide / tetrahydrofuran; water / 4 h / 0 °C
6.1: benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine / N,N-dimethyl-formamide / 24 h
7.1: lithium hydroxide; water / tetrahydrofuran / 2 h
8.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 12 h
With
palladium 10% on activated carbon; water; hydrogen; benzotriazol-1-ol; 1,2-dichloro-ethane; N-ethyl-N,N-diisopropylamine; HATU; sodium hydroxide; lithium hydroxide;
In
tetrahydrofuran; water; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/jm300771j