N'-(3-dimethylaminopropyl)-N-ethylcarbodiimide in N,N-dimethyl-formamide

1: (2S,3S,5S)-2-(2,6-dimethylphenoxyacetyl)amino-3-hydroxy-5-amino-1,6-diphenylhexane With 1H-imidazole in ethyl acetate T=20°C; 2: 2S-(1-tetrahydro-pyrimid-2-onyl)-3-methyl butanoyl chloride in ethyl acetate; N,N-dimethyl-formamide T=0 - 20°C; 13 h;

1H-imidazole in ethyl acetate; N,N-dimethyl-formamide T=0 - 20°C; Inert atmosphere; Reagent/catalyst;

1: With 1H-imidazole in ethyl acetate; N,N-dimethyl-formamide T=0 - 25°C; 13 h; 2: With hydrogenchloride in water; ethyl acetate; N,N-dimethyl-formamide T=10 - 15°C;

sodium hydrogencarbonate in water; ethyl acetate T=20 - 25°C; 1.16667 h;

1: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / |Inert atmosphere 2: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / |Inert atmosphere 3: 5 palladium on charcoal; ammonium formate / methanol / 50 °C / |Inert atmosphere 4: 1,4-dioxane / 1 h / 20 - 50 °C / |Inert atmosphere 5: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / |Inert atmosphere View Scheme

1: lithium chloride; lithium hydroxide hydrate; aluminum oxide / water / 5 h / -20 - -10 °C / pH 9.5 - 10.2 / |Inert atmosphere 2: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / |Inert atmosphere 3: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 4: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / |Inert atmosphere 5: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / |Inert atmosphere 6: 5 palladium on charcoal; ammonium formate / methanol / 50 °C / |Inert atmosphere 7: 1,4-dioxane / 1 h / 20 - 50 °C / |Inert atmosphere 8: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / |Inert atmosphere View Scheme

1: sodium hydroxide / tetrahydrofuran / 2 h / 2 - 10 °C / |Inert atmosphere 2: potassium tert-butylate / tetrahydrofuran / 18 h / 20 °C / |Inert atmosphere 3: thionyl chloride / tetrahydrofuran / 5.5 h / 4 - 20 °C / |Inert atmosphere 4: 1H-imidazole / ethyl acetate; N,N-dimethyl-formamide / 2 - 30 °C / |Inert atmosphere 5: 5 palladium on charcoal; ammonium formate / methanol / 50 °C / |Inert atmosphere 6: 1,4-dioxane / 1 h / 20 - 50 °C / |Inert atmosphere 7: sodium hydrogencarbonate / ethyl acetate; water / 0.58 h / 20 °C / |Inert atmosphere View Scheme

1: LiOH 2: EDAC; HOBt View Scheme

1: LiOH 2: EDAC; HOBt View Scheme