Trifluoroacetic acid → 3-Amino-3-methyl-N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide

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Reaction Steps

To a solution of 502 mg (1.34 mmol) of 3-t-butoxycarbonylamino-3-methyl- N-[2,3,4,5-tetrahydro-2-oxo-1H-benzazepin-3(R)-yl]butanamide (Example 1, Step I) in 3 mL of methylene chloride at 0° C. was added 0.160 mL (1.47 mmol) of anisole followed by 3 mL of trifluoroacetic acid. The mixture stirred at room temperature for 3 hours. All volatiles were removed under vacuum to give an oil which was dissolved in 10 mL of water. To this solution was added 268 mg (6.7 mmol) of sodium hydroxide and the resulting mixture was stirred until all the solids were dissolved. The solution was transferred to a separatory funnel and the aqueous layer was extracted with chloroform (3×50 mL). The combined organic extracts were washed with brine, dried over sodium surf ate and filtered. The solvent was removed under vacuum to afford 368 mg (100%) of the product as a white solid. 1H NMR (200 MHz, CDCl3): δ 1.27 (s, 6H), 1.95-2.30 (m, 2H), 2.37-2.75 (m, 3H), 2.80-3.02 (m, 1H), 3.48 (s, 2H), 4.52 (m, 1H), 6.97 (m, 1H), 7.1-7.27 (m, 3H), 7.98 (s, 1H), 8.29 (d, 7 Hz, 1H). FAB-MS: calculated for C15H21N3O2 275; found 276 (M+H, 100%).

Provenance & Evidence