Multi-step reaction with 9 steps
1: dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days
2: ammonium formate / 10percent Pd-C / methanol
3: dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days
4: 90.7 percent / 1N HCl, acetic acid / 1 h
5: 60.3 percent / NaHCO3, diphenyl phosphorazidate / dimethylformamide
6: 2N aq. NaOH / methanol
7: 78.8 percent / dicyclohexylcarbodiimide (DCCI), 1-hydroxybenzotriazole (HOBt), triethylamine / dimethylformamide / 1.) 4 deg C, 48 h, 2.) RT, 3 days
8: H2 / 5percent Pd-C
9: 51.2 percent / sodium cyanoborohydride / methanol / Ambient temperature
With
hydrogenchloride; sodium hydroxide; diphenyl phosphoryl azide; hydrogen; ammonium formate; sodium cyanoborohydride; sodium hydrogencarbonate; benzotriazol-1-ol; acetic acid; triethylamine; dicyclohexyl-carbodiimide;
palladium on activated charcoal;
In
methanol; N,N-dimethyl-formamide;
DOI:10.1021/jm00171a033