1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → BOC-Ala-Gly-OBzl

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

BOC-Ala-OH (94.6 g.), H-Gly-OBzl.TosOH (168.8 g.) and HOBT (67.6 g.) were dissolved in THF (450 ml.) and WSC (91.5 ml.) was added thereto, then stirred for 1 hour at 0° C. and overnight at room temperature. The reaction mixture was concentrated in vacuo and the residue was dissolved in ethyl acetate (800 ml.). 1 N HCl (500 ml.) was added, the precipitate was removed by filtration, and the ethyl acetate layer was washed with 1 N HCl (400 ml.), and twice with 5% sodium bicarbonate solution and water in this order, and, after drying with anhydrous magnesium sulfate, concentrated in vacuo. The residue was treated with n-hexane to obtain crude material (152.5 g.) Recrystallization was carried out twice by ethyl acetate - n-hexane to obtain BOC-Ala-Gly-OBzl (144 g., Yield: 85.7%, m.p.: 87° - 88.5° C., TLC: one spot, RF1 = 0.59).

Herkunft & Nachweise