Hydrochloric Acid → (2S)-2-amino-N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]butanamide

Participants

Reaction Steps

To a stirred solution of tert-butyl (1S)-1-({[5-chloro-2-(1H-tetraazol-1-yl)benzyl]amino}carbonyl)propylcarbamate (237 mg, 0.60 mmol) in EtOAc (3.5 mL) at rt was added 4 M HCl in dioxane (0.6 mL, excess). After 30 min, a small amount of MeOH was added to keep product in solution. After 3 h, another 0.6 mL of 4 M HCl/dioxane was added and continued to stir overnight at rt. Solvent was removed in vacuo to give the title compound as a foamy yellow solid. LCMS (M+H): 295.0. 1H NMR (400 MHz, CD3OD): δ 9.58 (s, 1 H), 8.79 (m, 1 H), 7.68 (d, J=2.4 Hz, 1 H), 7.58 (dd, J=2.0 Hz, 8.4 Hz, 1 H), 7.52 (d, J=8.4 Hz, 1 H), 4.30–4.29 (m, 2 H), 3.79 (app t, J=6.2 Hz, 1 H), 1.87–1.80 (m, 2 H), 0.97 (t, J=7.6 Hz, 3 H).

Provenance & Evidence