Multi-step reaction with 10 steps
1: 91 percent
2: 88 percent / 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride, 1-hydroxybenzotriazole, NaHCO3 / dimethylformamide / 10 h / 25 °C
3: 85 percent / trifluoroacetic acid / CH2Cl2 / 1 h / 25 °C
4: 88 percent / EDCI, HOBt / dimethylformamide / 12 h / 25 °C
5: 90 percent / aq. LiOH / tetrahydrofuran; methanol / 3 h / 25 °C
6: 86 percent / EDCI / CH2Cl2 / 4 h / 25 °C
7: 81 percent / tetrahydrofuran / 12 h / 50 °C
8: 92 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h / 25 °C
9: 100 percent / HCl / ethyl acetate / 1.) 0 deg C, 10 min, 2.) 25 deg C, 50 min
10: 65 percent / NaHCO3, diphenylphosphoryl Azide / dimethylformamide / 48 h / 4 °C
With
hydrogenchloride; lithium hydroxide; diphenylphosphoranyl azide; sodium hydrogencarbonate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trifluoroacetic acid;
In
tetrahydrofuran; methanol; dichloromethane; ethyl acetate; N,N-dimethyl-formamide;
DOI:10.1021/ja00133a010