hydrogenchloride; acetic acid; methoxybenzene 1.5 h;

1: N-methylmorpholine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) to r. t., 1 h 2: HCl / methanol / 2 h View Scheme

1: N-hydroxybenzotriazole, triethylamine, dicyclohexylcarbodiimide / dimethylformamide 2: HCl /acetic acid/ anisole / 1.5 h View Scheme

hydrogenchloride in methanol 2 h;

1: N-methylmorpholine / CH2Cl2 / 0.25 h / 0 °C 2: N-methylmorpholine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) to r. t., 1 h 3: HCl / methanol / 2 h View Scheme

1: N-methylmorpholine, 2,6-lutidine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r. t., 1 h 2: 86 percent / HCl / methanol / 0.5 h / 35 °C 3: N-methylmorpholine, 2,6-lutidine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r. t., 1 h 4: HCl / methanol / 0.5 h / 35 °C 5: N-methylmorpholine, 2,6-luditine / CH2Cl2; dimethylformamide / 1.) 0 deg C, 1 h, 2.) r. t., 1 h 6: 91 percent / aq. NaOH / dimethylformamide / 6 h 7: 40 percent / aq. HCl / dioxane / 6 h View Scheme

1: 89 percent / DCC, HOBt 2: 91 percent / aq. NaOH / dioxane 3: acid hydrolysis View Scheme