Hydrochloric Acid → 2-(S)-amino-N-[3-(1H-indol-3-yl)-propyl]-butyramide

Participants

Reaction Steps

A 20 mL cintillation vial was charged with 3-[3-(2-(S)-tert-butoxycarbonylamino-butyrylamino)-propyl]-indole-1-carboxylic acid tert-butyl ester (280 mg, 0.61 mmol), dichloromethane (3.6 mL), and 1M hydrogen chloride in diethyl ether (3.0 mL). The resulting mixture was stirred at room temperature for 4 h, then concentrated in-vacuo and the residue placed under high vacuum overnight to yield 2-(S)-amino-N-[3-(1H-indol-3-yl)-propyl]-butyramide. 1H NMR (300 MHz, CD3OD) δ 7.51 (d, J=7.8 Hz, 1H), 7.32 (d, J=8.0 Hz, 1H), 6.95-7.09 (m, 3H), 3.11-3.39 (m, 3H), 2.77-2.82 (m, 2H), 1.78-2.01 (m, 4H), and 0.94 (t, J=7.4 Hz, 3H); MS (ES+) 260 (M+1).

Provenance & Evidence