Multi-step reaction with 11 steps
1.1: NaH / dimethylformamide / 0.17 h / 0 °C
1.2: 74 percent / dimethylformamide / 5 h / 20 °C
2.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
3.1: 1.95 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C
4.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
5.1: 2.6 g / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / CH2Cl2 / 18 h / 20 °C
6.1: trifluoroacetic acid / CH2Cl2 / 1 h / 20 °C
7.1: 411 mg / Et3N; 1-hydroxybenzotriazole hydrate; water soluble carbodiimide hydrochloride / dimethylformamide / 18 h / 20 °C
8.1: 96 percent / H2 / 10 percent Pd/C / dimethylformamide / 18 h / 20 °C
9.1: 75 percent / Et3N; SO3*pyridine / dimethylsulfoxide / 1 h / 20 °C
10.1: 2.3 mg / NaBH4 / methanol / 2 h / 20 °C
11.1: 6N HCl / 18 h / 105 °C
With
hydrogenchloride; sodium tetrahydroborate; pyridine-SO3 complex; hydrogen; sodium hydride; 1-hydroxybenzotriazol-hydrate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; trifluoroacetic acid;
palladium on activated charcoal;
In
methanol; dichloromethane; dimethyl sulfoxide; N,N-dimethyl-formamide;
DOI:10.7164/antibiotics.54.1004