Diisopropylethylamine → HCID 21341520, compound

Participants

Reaction Steps

A mixture of Boc-D-homophenylalanine (3.0 g), methoxymethylamine hydrochloride (1.15 g), PyBrop (5 g); diisopropylethylamine (5.6 mL), and dichloromethane (10 mL) was stirred at 25° C. for 10 h., and the reaction mixture was poured into ethyl acetate and washed successively with water, 1N HCl, sat. sodium bicarbonate and brine. The combined extracts was dried (Na2SO4) and concentrated in vacuo. Further purification by chromatography over silica gel (45% ethyl acetate/hexane) afforded titled compound (6.76 g) as a white solid: 1H NMR (400 MHz, CDCl3) δ 1.46 (s, 9H), 1.85 (m, 1H), 2.04 (m, 1H), 2.72 (m, 2H), 3.17 (s, 3H), 3.63 (s, 3H), 4.69 (m, 1H), 5.25 (bd, 1H, NH), 7.20 (m, 3H), and 7.28 (m, 2H).

Provenance & Evidence