(1S,3S,5S)-2-Azabicyclo(3.1.0)hexane-3-carboxamide → benzyl N-[(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo ethyl]carbamate

Participants

Reaction Steps

Path B: Coupling reaction of (1S,3S,5S)-2-azabicyclo[3.1.0]hexane-3-carboxamide or its salts of Formula-III with (2S)-2-{[(benzyloxy)carbonyl]amino}-2-(3-hydroxyadamantan-1-yl)acetic acid of formula-XIV to give benzyl N-[(1S)-2-[(1S,3S,5S)-3-carbamoyl-2-azabicyclo[3.1.0]hexan-2-yl]-1-(3-hydroxyadamantan-1-yl)-2-oxo-ethyl]carbamate of formula-XV, can be carried out in a suitable solvent, for example, tetrahydrofuran, N,N-dimethyl formamide, 1,4-dioxane or ethyl acetate using a coupling agent for example, 1,3-dicyclohexyl carbodiimide (DCC), 1-ethyl-3-(3′-dimethylaminoporpyl)carbodiimide (EDAC), 1-propane phosphonic acid cyclic anhydride or N-[(dimethyl amino)-1H-1,2,3-triazolo[4,5-b]pyridylmethylene]-N-methyl methanaminium hexafluoro phosphate N-oxide (HATU) and optionally a catalyst, for example, 1-hydroxybenzotriazole (HOBT) or 7-aza-1-hydroxy benzotriazole (HOAt) and optionally, with a base, for example, N,N-dimethylamino pyridine (DMAP), triethylamine, N,N-diisopropyl ethyl amine, or N-methyl morpholine.

Provenance & Evidence