Diisopropylethylamine → HCID 21341520, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of N-tert-butoxycarbonyl-D-homophenylalanine (3.0 g, 10.7 mmol), methoxymethylamine hydrochloride (1.15 g, 1.1 eq.), PyBrop (5 g, 1 eq.), diisopropylethylamine (5.6 mL, 3 eq.) and dichloromethane (10 mL) was stirred at 25° C. for 10 hours, and the reaction mixture was poured into ethyl acetate and washed successively with water, 1 N 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 the title 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