Acetic Acid → HCID 20662286, compound

Participants

Reaction Steps

A cold solution (0° C.) of the above amine (3 g, 8.6 mmol), in methanol (20 ml), was treated sequentially with acetic acid (345 μl, 6 mmol) and phenylacetaldehyde (1.2 ml, 10 mmol). Then a solution of sodium cyanoborohydride (2.7 g, 43 mmol) in methanol (10 ml) was added to the mixture slowly. The reaction was stirred for additional 30 minutes and the solvent was removed in vacuo. The residue was dissolved in ethyl acetate and washed with aqueous sodium bicarbonate, and purified by chromatography (silica gel, hexane/ethyl acetate) to afford Nα-(phenethyl)ornithine 3-phenylpropylamide (2.64 g): 1H NMR (400 MHz, CD3OD) δ1.4 (s, 9H), 1.45-1.8 (m, 6H), 2.6 (t, J=6.4 Hz, 2H), 2.65-2.8 (m, 4H), 3.02-3.2 (m, 5H), and 7.1-7.3 (m, 10H).

Provenance & Evidence