Hydrochloric Acid → 3-(Benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylic acid

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Reaction Steps

A mixture of ethyl 3-(benzyloxy)-4-oxo-6,7,8,9-tetrahydro-4H-7,10-ethanopyrimido[1,2-a][1,3]diazepine-2-carboxylate (0.5491 g, 1.486 mmol) and LiOH.H2O (0.071 g, 2.97 mmol) in ethanol (12 mL) and water (3.00 mL) was stirred at room temperature for 6 h. The mixture was acidified with concentrated HCl and the product was extracted with ethyl acetate. The organic phase was washed with brine, then dried (Na2SO4), filtered and concentrated to give the title compound as a white solid (0.4521 g, 89% yield). 1H NMR (500 MHz, CD3OD) δ: 7.53-7.49 (2H, m), 7.42-7.36 (3H, m), 5.27 (2H, d, J=15.3 Hz), 4.11-4.00 (4H, m), 3.96 (2H, d, J=14.0 Hz), 3.17-3.13 (1H, m), 2.45-2.39 (2H, m), 2.10-2.03 (2H, m). LCMS (M+H) calcd for C18H20N3O4: 342.14; found: 342.20.

Provenance & Evidence