反应详情

In 80 ml of the tetrahydrofuran were dissolved 1.00 g of DL-trans-benzylhydrogenepoxysuccinate, 1.70 g of N-L-leucyl-N'-benzyloxycarbonyl-1,7-diaminoheptane, 0.73 g of 1-hydroxybenzotriazole and 0.55 g of N-methylmorpholine. To the solution was slowly added 0.95 g of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride under ice-cooling with stirring. The mixture was stirred for 2 hours under ice-cooling and then for 2 hours at room temperature. The solution was concentrated under reduced pressure and admixed with 100 ml of ethyl acetate and 100 ml of water and the mixture was shaken vigorously. The ethyl acetate layer was separated and washed successively with a 10% aqueous hydrochloric acid solution, an aqueous saturated bicarbonate solution and an aqueous saturated sodium chloride solution and concentrated to dryness. The resulting residue was purified by column chromatography on silica gel (chloroform:acetone=10:1) and recrystallized from ethyl acetate-n-hexane to give 1.50 g of N-[N-DL-3-trans-benzyloxycarboxyloxirane-2-carbonyl)-L-leucyl]-N'-benzyloxycarbonyl-1,7-diaminoheptane m.p. 134° C. Yield: 67%.

1. temperaturecooling
2. stirringThe mixture was stirred for 2 hours under ice-
3. temperaturecooling
4. concentrationThe solution was concentrated under reduced pressure
5. stirringthe mixture was shaken vigorously
6. customThe ethyl acetate layer was separated
7. washwashed successively with a 10% aqueous hydrochloric acid solution
8. concentrationan aqueous saturated bicarbonate solution and an aqueous saturated sodium chloride solution and concentrated to dryness
9. customThe resulting residue was purified by column chromatography on silica gel (chloroform:acetone=10:1)
10. customrecrystallized from ethyl acetate-n-hexane