Methanol → (S)-2-amino-N-(3-(1-methyl-1H-indol-2-yl)propyl)butanamide

Participants

Reaction Steps

A 20 mL cintillation vial was charged with N-(3-(1-methyl-1H-indol-2-yl)propyl)-2-(S)-(2,2,2-trifluoro-acetylamino)butanamide (57.0 mg, 0.154 mmol), tetrahydrofuran (0.77 mL), and methanol (0.20 mL). 3N Sodium hydroxide (0.15 mL, 0.450 mmol) was added and the resulting mixture stirred at room temperature for 18 h. The resulting mixture was then diluted with dichloromethane and extracted with 1 N HCl. The aqueous layer was neutralized to pH 8 and extracted with dichlormethane. The organic layer was dried with MgSO4, filter, and concentrate in vacuo. The resulting solid was taken up in water and lyophilized to yield (S)-2-amino-N-(3-(1-methyl-1H-indol-2-yl)propyl)butanamide. 1H NMR (300 MHz, CD3OD) δ 7.42 (d, J=7.7 Hz, 1H), 7.29 (d, J=8.0 Hz, 1H), 7.05-7.11 (m, 1H), 6.94-7.02 (m, 1H), 6.23 (s, 1H), 3.60-3.75 (m, 4H), 3.31-3.46 (m, 2H), 2.69-2.86 (m, 2H), 1.91-2.03 (m, 2H), 1.71-1.89 (m, 2H), and 1.02 (t, J=7.4 Hz, 3H); MS (ES+) 274 (M+1).

Provenance & Evidence