trifluoroacetic acid in dichloromethane T=20°C; 1 h;

1: With sodium hydroxide in methanol; water; N,N-dimethyl-formamide T=70°C; 2: With hydrogenchloride; ammonium chloride; triethylamine in water; N,N-dimethyl-formamide T=20°C; 0.0833333 h; 3: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in water; N,N-dimethyl-formamide T=20°C; 120 h;

1: With ammonium chloride; triethylamine in N,N-dimethyl-formamide 0.166667 h; 2: With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride in N,N-dimethyl-formamide 96 h; Product distribution / selectivity;

1.1: pyridine / acetonitrile / 0 - 20 °C / Cooling with ice 2.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 2.2: 1 h / -78 - 20 °C 3.1: potassium carbonate; methanol / water / 2 h / 20 °C 4.1: sodium hydroxide / N,N-dimethyl-formamide; water; methanol / 70 °C 4.2: 0.08 h / 20 °C 4.3: 120 h / 20 °C View Scheme

1.1: potassium carbonate; methanol / water / 2 h / 20 °C 2.1: sodium hydroxide / N,N-dimethyl-formamide; water; methanol / 70 °C 2.2: 0.08 h / 20 °C 2.3: 120 h / 20 °C View Scheme

1.1: diisopropylamine; n-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 1 h / -78 - 20 °C 2.1: potassium carbonate; methanol / water / 2 h / 20 °C 3.1: sodium hydroxide / N,N-dimethyl-formamide; water; methanol / 70 °C 3.2: 0.08 h / 20 °C 3.3: 120 h / 20 °C View Scheme