Triethylamine → Benzyl (2-((4-fluorobenzyl)carbamoyl)-3-hydroxy-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)carbamate

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Reaction Conditions

Reaction Steps

A mixture of ethyl 10-(((benzyloxy)carbonyl)amino)-3-hydroxy-4-oxo-4,6,7,8,9,10-hexahydro-7,10-ethanopyrimido[1,2-a]azepine-2-carboxylate (5.00 g, 11.70 mmol), (4-fluorophenyl)methanamine (2.67 mL, 23.39 mmol) and Et3N (3.26 mL, 23.39 mmol) in ethanol (78 mL) was stirred at 90° C. for 16 h, cooled and concentrated. The resulting pale yellow foam was dissolved in ethyl acetate and washed with 1N HCl. The organic phase was washed with brine, dried (Na2SO4), filtered and concentrated. The residue was taken up in hot ethyl acetate and hexane was added until the solution became slightly cloudy. After cooling, the title compound was collected by filtration as a white solid (4.8203 g, 81% yield). 1H NMR (500 MHz, DMSO-D6) δ: 10.25 (s, 1H), 7.52 (s, 1H), 7.34-7.40 (m, 8H), 7.15-7.21 (m, 2H), 5.72 (s, 1H), 4.91 (s, 2H), 4.40 (d, 2H, J=6.4 Hz), 4.15 (s, 2H), 2.48-2.52 9 m, 2H), 2.02-2.08 (m, 2H), 1.94-1.98 (m, 2H), 1.63-1.70 (m, 2H). LCMS (M+H)=507.42.

Provenance & Evidence