Benzyl succinimido carbonate → HCID 22877443, compound

Participants

Reaction Steps

To a solution of 33 mg (0.12 mmol) of 2-amino-2-methyl-N-[7-fluoro-2,3,4,5-tetrahydro-2-oxo-1H-1-benzazepin-3(R)-yl]propanamide (Step D) in 1 mL of methylene chloride was 32 mg (0.13 mmol) of N-(benzyloxycarbonyloxy)succinimide. The soution was stirred at room temperature for 24 hours then quenched with 5 drops of 33% aqueous ammonium hydroxide. The solvent was removed under vacuum and the residue was purified by flash column chromatography on silica gel eluting with ethyl acetate/hexanes (75:25) to afford 25 mg (46%) of the product as an off-white solid. 1H NMR (400 MHz, CDCl3): δ 1.48 (s, 3H), 1.50 (s, 3H), 1.82 (m, 1H), 2.56 (m, 1H), 2.71 (m, 1H), 2.86 (m, 1H), 4.42 (m, 1H), 5.05 (s, 2H), 5.43 (s, 1H), 6.90 (m, 2H), 7.09 (d, 8 Hz, 1H), 7.30 (m, 5H), 8.09 (s, 1H). FAB-MS: calculated for C22H24FN3O4 413; found 414 (M+H, 100%).

Provenance & Evidence