Methanol → HCID 86630336, compound

Participants

Reaction Steps

To a solution of 90.1 mg (0.258 mmol) of β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester hydrochloride in methylenechloride (1 mL), 100.0 mg (0.774 mmol) of N,N-diisopropylethylamine and 37.2 mg (0.285 mmol) of 2-furoyl chloride were added with stirring under ice cooling and the reaction mixture was stirred for 0.5 hour. Methanol (0.2 mL) was added and the reaction mixture was stirred at room temperature, and then concentrated under reduced pressure. Chloroform (25 mL) was added to the residue, and then the mixture was washed with 0.5M hydrochloric acid (3×5 mL) and 5% aqueous sodium hydrogencarbonate solution (3×5 mL). The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure, whereby 127 mg of the crude product was obtained. The crude product was purified by silica gel column chromatography [silica gel 7.5 g, chloroform, methanol-chloroform (1:100)], to give 103.2 mg of 2-furoyl-β-cyclohexyl-L-alanyl-glycyl-glycine ethyl ester as a colorless oil (yield 98%)

Provenance & Evidence