Water → HCID 73895619, compound

Participants

Reaction Steps

A mixture of 10 mL diethyl ether, 2 mL water, and 150 mg magnesium carbonate was cooled in an ice bath and 0.83 mL (4.16 mmol) 5M cyanogen bromide in acetonitrile was added with stirring. A solution of (D)-prolyl-leucine benzyl ester (883 mg, 2.77 mmol) in 17 mL diethyl ether was added over the course of 10 minutes. Another 0.20 mL (1.0 mmol) of 5M cyanogen bromide in acetonitrile was then added and the mixture was stirred at room temperature for 30 minutes. The organic phase was decanted and the aqueous phase extracted twice with diethyl ether. The combined ether phase was washed with 1N HCl, water, and saturated sodium bicarbonate, then dried over magnesium sulfate. Filtration and evaporation of solvent gave the crude product that was purified by flash chromatography on silica gel, eluting with 2% methanol/dichloromethane. N-cyano-(D)-prolyl-leucine benzyl ester (11) was isolated as a pale yellow oil.

Provenance & Evidence