Diisopropylethylamine → HCID 86757004, compound

Participants

Reaction Steps

A cold solution (0° C.) of N-Boc-homophenylalanine (221 mg), diisopropylethylamine (228 μl), and anhydrous tetrahydrofuran (4 ml) was treated with PyBrop (398 mg), followed by the addition of a solution of Nδ-Boc-Nα-methylornithine 3-phenylpropylamide (228 mg) in tetrahydrofuran (3 ml). The resulting solution was stirred for overnight. The precipitate was filtered and the solid was washed with ethyl acetate. The filtrate was concentrated in vacuo and the product purified by silica gel chromatography (hexane/ethyl acetate) to give N-Boc-homophenylalanyl-Nδ-Boc-Nα-methylornithine 3-phenylpropylamide (260 mg): 1H NMR (400 MHz, CDCl3) δ1.43 (s, 18H), 1.7-2.0 (m, 8H), 2.58 (t, J=6.4 Hz, 2H), 2.6-2.85 (m, 5H), 3.0-3.4 (m, 4H), 4.4-4.5 (m, 1H), 4.9-5.0 (m, 1H), and 7.1-7.3 (m, 10H).

Provenance & Evidence