Piperidine → HCID 88140646, compound

Participants

Reaction Steps

525 mg (1.1 mmol) of N2-[(9-fluorenyl)methoxycarbonyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide were dissolved in 20 ml of dichloromethane and 5 ml of piperidine and the mixture was stirred at room temperature for 30 minutes. The mixture was evaporated to dryness and the residue was chromatographed on silica gel using firstly ethyl acetate/petrol (1:1) and then methanol/dichloromethane (1:9) for the elution. Evaporation of the dichloromethane solution gave a gum which was added to a solution of 363 mg (1.03 mmol) of N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-leucine, 149 mg (1.1 mmol) of hydroxybenzotriazole and 288 mg (1.5 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride in 15 ml of dichloromethane. The mixture was stirred for 18 hours, then washed with 2M hydrochloric acid and saturated sodium bicarbonate solution, dried over magnesium sulphate and evaporated to dryness. The residue was chromatographed on silica gel using ethyl acetate/petrol (1:2) for the elution to give 501 mg of N2-[N-[(9-fluorenyl)methoxycarbonyl]-3-methyl-L-valyl]-N1-[1(S)-(dimethoxymethyl)-3-butynyl]-L-leucinamide as a white foam. MS: m/e 592.3 [M+H]+, 560.3 [M+H-MeOH]+.

Provenance & Evidence