反应详情

3-Formylindol-1-ylacetic acid was prepared and coupled to the beads above according to the process of EP 0 801 083 A2 (Estep et al.) using diisopropyl carbodiimide, N,N-diisopropylethylamine, and N-hydroxybenzotriazole in DMF/CH2Cl2. Benzylamine was reductively coupled to this bead-linker using sodium cyanoborohydride in 0.5M acetate buffer, pH 5, by the procedure in the same document. The product was then acetylated using acetic anhydride/triethylamine. The acetylated amine was released from the resin by treatment with 50% TFA/CH2Cl2 for 4 hours. The filtrate was evaporated to dryness and the residue evaluated by NMR and mass spectroscopy to show that the major product was N-benzylacetamide. This example demonstrates the feasibility of conducting solid phase synthesis using azlactone-functionalized beads.

1. customThe filtrate was evaporated to dryness
2. customsolid phase synthesis