Water → 3-(Benzyloxy)-10-(((benzyloxy)carbonyl)amino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylic acid

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Reaction Steps

To a solution of ethyl 3-(benzyloxy)-10-(((benzyloxy)carbonyl)amino)-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate, Intermediate 3 (250 mg, 0.483 mmol) in EtOH (5 mL) was added water (1.250 mL) followed by LiOH—H2O (20.27 mg, 0.483 mmol) and the mixture was stirred at room temp for 16 h. Water (10 mL) was then added and the mixture was extracted with ether (100 mL). The aqueous layer was then acidified with 1N HCl and then extracted with ethyl acetate (2×100 mL), washed with brine, dried (Na2SO4), filtered and concentrated to afford the title compound (180 mg, 76% yield) as a light yellow solid. 1H NMR (500 MHz, CDCl3) δ: 7.51 (d, 2H, J=6.71 Hz), 7.30-7.40 (m, 9H), 5.46 (s, 2H), 5.06 (s, 2H), 4.10-4.15 (m, 2H), 2.47-2.61 (m, 3H), 2.03-2.11 (m, 2H), 1.91-2.01 (m, 2H), 1.63-1.73 (m, 2H). LCMS (M+H)=490.23.

Provenance & Evidence