1: 43 percent / McIlvaine's buffer cont. EDTA; thiothreitol / papain (from Carica papaya) / acetonitrile; dimethylformamide / 36 h / 20 °C / pH 6.2 / Enzymatic reaction 2: 81 percent / conc. HCl / methanol / 8 h / Heating View Scheme

1: 43 percent / McIlvaine's buffer cont. EDTA; thiothreitol / papain (from Carica papaya) / acetonitrile; dimethylformamide / 36 h / 20 °C / pH 6.2 / Enzymatic reaction 2: 81 percent / conc. HCl / methanol / 8 h / Heating View Scheme

thiothreitol; McIlvaine's buffer cont. EDTA; papain (from Carica papaya) in N,N-dimethyl-formamide; acetonitrile T=20°C; pH=6.2; 36 h; Enzymatic reaction;

1: 43 percent / McIlvaine's buffer cont. EDTA; thiothreitol / papain (from Carica papaya) / acetonitrile; dimethylformamide / 36 h / 20 °C / pH 6.2 / Enzymatic reaction 2: 81 percent / conc. HCl / methanol / 8 h / Heating View Scheme

1: With hydroxylamine hydrochloride; potassium carbonate in 1,4-dioxane; water T=20°C; 12 h; 2: With 3-(dimethylamino)-n-propylamine in 1,4-dioxane; water T=20°C; 1 h;

1,8-diazabicyclo[5.4.0]undec-7-ene in dichloromethane T=0 - 20°C; Title compound not separated from byproducts;

1.1: 93 percent / Zn / acetic acid / 0.5 h / 20 - 30 °C 2.1: SOCl2 / methanol / 20 h / 20 °C 3.1: K2CO3; NH2OH*HCl / dioxane; H2O / 12 h / 20 °C 3.2: 18.5 g / 3-dimethylaminopropylamine / dioxane; H2O / 1 h / 20 °C View Scheme

1.1: 74 percent / KMnO4; Na2CO3 / H2O / 50 h / 50 °C 2.1: 99 percent / NH2OH*HCl / H2O / 0.33 h / 45 °C 3.1: 93 percent / Zn / acetic acid / 0.5 h / 20 - 30 °C 4.1: SOCl2 / methanol / 20 h / 20 °C 5.1: K2CO3; NH2OH*HCl / dioxane; H2O / 12 h / 20 °C 5.2: 18.5 g / 3-dimethylaminopropylamine / dioxane; H2O / 1 h / 20 °C View Scheme

1.1: SOCl2 / methanol / 20 h / 20 °C 2.1: K2CO3; NH2OH*HCl / dioxane; H2O / 12 h / 20 °C 2.2: 18.5 g / 3-dimethylaminopropylamine / dioxane; H2O / 1 h / 20 °C View Scheme