Hydrochloric Acid → Ethyl 10-amino-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate hydrochloride

Participants

Reaction Steps

To a mixture of ethyl 10-(((benzyloxy)carbonyl)amino)-4-oxo-3-((phenylcarbonyl)oxy)-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (16 g, 30.1 mmol) in ethyl acetate (300 mL) and methanol (150 mL) was added 1N HCl (31.6 mL, 31.6 mmol) followed by Pd/C (3.20 g, 3.01 mmol) and the mixture was stirred under balloon hydrogen atmosphere for 2 h. The mixture was then filtered through a pad of CELITE® and the pad was thoroughly washed with ethyl acetate. The filtrate was concentrated under reduced pressure and dried under high vacuum overnight to afford the title compound (12.75 g, 98% yield),as an off-white solid. 1H NMR (500 MHz, CDCl3) δ: 8.11-8.16 (2 H, m), 7.62 (1 H, t, J=7.40 Hz), 7.48 (2 H, t, J=7.78 Hz), 4.19 (2 H, q, J=7.11 Hz), 4.13 (2 H, d, J=3.51 Hz), 2.71-2.83 (2 H, m), 2.53 (1 H, brs), 2.32-2.46 (2 H, m), 2.01-2.13 (2 H, m), 1.74-1.85 (2 H, m), 1.03 (3 H, t, J=7.03 Hz). LCMS (M+H)=398.10.

Provenance & Evidence