Triethylamine → N-(5-phthalimidopentanoyl)-L-alanyl-D-isoglutamine benzyl ester

Beteiligte Stoffe

Reaktionsbedingungen

Reaktionsschritte

L-alanyl-D-isoglutamine benzyl ester hydrochloride (548 mg, 1.6 mmoles) and 5-phthalimidopentanoic acid (400 mg, 1.6 mmoles) were dissolved in N,N-dimethylformamide (8 ml). The solution was cooled to 0° C. and diphenylphosphoryl azide (495 mg, 1.8 mmoles) and triethylamine (323 mg, 3.2 mmoles) were added thereto. The reaction mixture was stirred for 1 hour at 0° C. and for 24 hours at room temperature. The reaction mixture was diluted by ethyl acetate (40 ml) and the organic phase was washed successively with citric acid (0.52M; 3×10 ml), water (3×10 ml), saturated NaCl solution (3×10 ml), saturated NaHCO3 solution (3×10 ml), water (3×10 ml) and saturated NaCl solution (3×10 ml). The organic phase was dried with MgSO4 and filtered, the filtrate was evaporated and the product was precipitated from n-hexane/diethyl ether. The compound was filtered off and crystallized from acetone.

Herkunft & Nachweise