Multi-step reaction with 12 steps
1.1: H2O / 12 h / 25 °C / pH 8
2.1: 91 percent / benzene; methanol / 0 °C
3.1: 91 percent / HCl / ethyl acetate / 0.5 h / 25 °C
4.1: HOAt; EDCI / CH2Cl2 / 0.25 h / 0 °C
4.2: 78 percent / CH2Cl2 / 12 h
5.1: 100 percent / HCl / ethyl acetate / 0.5 h / 25 °C
6.1: 68 percent / HOAt; EDCI; NaHCO3 / CH2Cl2 / 12 h / 0 °C
7.1: 100 percent / aq. LiOH / tetrahydrofuran; methanol / 1.5 h / 25 °C
8.1: HOAt; EDCI / CH2Cl2 / 15 h / -20 °C
8.2: 49 percent / CH2Cl2 / 4 h
9.1: 100 percent / Zn; 90percent aq. AcOH / 2 h / 0 °C
10.1: 83 percent / HOAt; EDCI / CH2Cl2 / 6 h / 0 °C
11.1: Zn; 90percent aq. AcOH / 2 h / 0 °C
12.1: I2 / CH2Cl2; methanol / 2 h / 25 °C
With
hydrogenchloride; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; iodine; sodium hydrogencarbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; zinc;
In
tetrahydrofuran; methanol; dichloromethane; water; ethyl acetate; benzene;
DOI:10.1021/ja003602r