Hydrochloric Acid → HCID 53252317, compound

Participants

Reaction Conditions

Reaction Steps

A 200 mL round bottom flask was charged with (S)-methyl 2-(3-(2-(tert-butoxycarbonylamino)butanamido)propyl)-1H-indole-5-carboxylate (1.67 g, 4.00 mmol), tetrahydrofuran (20 mL), and methanol (5.3 mL). 3N Sodium hydroxide (4.0 mL, 12.0 mmol) was added and the resulting mixture stirred and heated to 50° C. for 8 h. The resulting mixture was then cooled to room temperature and acidified with 1N hydrochloric acid. The resulting mixture was extracted two times with ethyl acetate (400 mL). The organic layer was dried with MgSO4, filtered, and concentrated in vacuo to yield (S)-2-(3-(2-(tert-butoxycarbonylamino)butanamido)propyl)-1H-indole-5-carboxylic acid. 1H NMR (300 MHz, CD3OD) δ 8.20 (s, 1H), 7.75 (d, J=7.0 Hz, 1H), 7.32 (d, J=8.6 Hz, 1H), 6.31 (s, 1H), 3.94-4.10 (m, 1H), 3.22-3.34 (m, 2H), 2.80-2.85 (m, 2H), 1.61-2.08 (m, 4H), 1.46 (s, 9H), and 0.93-1.03 (m, 3H); MS (ES+) 403 (M+1).

Provenance & Evidence