N,N'-Dicyclohexylurea → 2-((tert-butoxy)carbonylamino)-3-hydroxy-N-(4-methyl-2-oxo(2H-chromen-7-yl))propanamide

Participants

Reaction Steps

Briefly, 1.1 mmol N-BOC-L-Serine (Fluka) is dissolved in 2 ml methylene chloride. Then 1.1 mmol 7-Amino-4-methylcoumarin and 1.2 mmol hydroxybenztriazole are added with stirring. Over a period of 30 minutes, a solution of 1.3 mmol dicyclohexyl carbodiimide in 1.4 ml methylene chloride is added dropwise. The reaction is stirred at room temperature for 20 hours, during which time a precipitate of dicyclohexylurea forms. The precipitate is removed by filtration and washed with methylene chloride. The combined solutions (filtrates) are evaporated under reduced pressure and the residue chromatographed over silica gel with methylene chloride--ethylacetate as the eluent yielding 2-((tert-butoxy)carbonylamino)-3-hydroxy-N-(4-methyl-2-oxo(2H-chromen-7-yl))propanamide.

Provenance & Evidence