Methyl N-(triethylammoniosulfonyl)carbamate → N'-(3-(Benzyloxy)-2-(5-(4-fluorobenzyl)-1,3-oxazol-2-yl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide

Participants

Reaction Steps

To a mixture of N′-(3-(benzyloxy)-2-((3-(4-fluorophenyl)-2-oxopropyl)carbamoyl)-4-oxo-6,7,8,9-tetrahydro-7,10-ethanopyrimido[1,2-a]azepin-10(4H)-yl)-N,N-dimethylethanediamide, Intermediate 16 (125 mg, 0.207 mmol) in THF (8 mL) was added Burgess Reagent (345 mg, 1.450 mmol) and the mixture heated to reflux for 5 h. The mixture was then cooled, concentrated and purified by preparative HPLC to afford the title compound (65 mg, 0.111 mmol, 53.6% yield) as a white solid. 1H NMR (500 MHz, CDCl3) δ ppm 9.24 (1H, s), 7.38-7.42 (2H, m), 7.30-7.34 (3H, m), 7.18-7.23 (2H, m), 7.11 (1H, s), 6.99-7.04 (2H, m), 5.38 (2H, s), 4.18 (2H, d, J=3.66 Hz), 4.02 (2H, s), 3.30 (3H, s), 3.03 (3H, s), 2.88-2.96 (2H, m), 2.54 (1H, br. s.), 1.94-2.10 (4H, m), 1.71-1.80 (2H, m). LCMS (M+H)=586.31.

Provenance & Evidence