Methanol → HCID 86630336, compound

Participants

Reaction Steps

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

Provenance & Evidence