1: With hydroxylamine hydrochloride; sodium methylate in methanol T=0°C; 0.333333 h; 2: (2S,3R)-3-hydroxy-2-(4-(4-morpholin-4-ylmethylphenylethynyl)benzoylamino)butyric acid methyl ester in tetrahydrofuran; methanol T=0 - 20°C; 5 h;

potassium cyanide; hydroxylamine in tetrahydrofuran; methanol; water T=20°C; 18 h;

1.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / acetonitrile / 0.5 h / 20 °C / |Inert atmosphere 1.2: 18 h / 20 - 100 °C / |Inert atmosphere; |Sealed tube 2.1: sodium hydroxide / ethanol / 18 h / 20 °C 3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C 3.2: 18 h / 20 °C 4.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 5.1: tetrahydrofuran; acetic acid / 0.08 h / 20 °C / |Inert atmosphere 5.2: 4 h / 20 °C / |Inert atmosphere 6.1: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 18 h / 20 °C View Scheme

1.1: sodium hydroxide / ethanol / 18 h / 20 °C 2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C 2.2: 18 h / 20 °C 3.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 4.1: tetrahydrofuran; acetic acid / 0.08 h / 20 °C / |Inert atmosphere 4.2: 4 h / 20 °C / |Inert atmosphere 5.1: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 18 h / 20 °C View Scheme

1.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine / tetrahydrofuran / 1 h / 20 °C 1.2: 18 h / 20 °C 2.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 3.1: tetrahydrofuran; acetic acid / 0.08 h / 20 °C / |Inert atmosphere 3.2: 4 h / 20 °C / |Inert atmosphere 4.1: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 18 h / 20 °C View Scheme

1.1: triethylamine; copper(l) iodide; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran / 3 h / 20 °C / |Inert atmosphere 2.1: tetrahydrofuran; acetic acid / 0.08 h / 20 °C / |Inert atmosphere 2.2: 4 h / 20 °C / |Inert atmosphere 3.1: hydroxylamine; potassium cyanide / tetrahydrofuran; methanol; water / 18 h / 20 °C View Scheme