1,2-Dichloroethane → N-[5-chloro-2-(1H-tetraazol-1-yl)benzyl]-L-prolinamide

Participants

Reaction Steps

The title compound was prepared essentially according to the EDC coupling procedure described in Example 26 using 1-[2-(1H-tetraazol-1-yl)phenyl]methanamine (Example 1, 55 mg, 0.31 mmol) and Boc-L-proline (67 mg, 0.31 mmol) followed by purification of the intermediate (silica gel chromatography, 50%–70% EtOAc/hexanes) and deprotection using 4.0 M HCl in dioxane. The hydrochloride salt of the title compound was isolated as a colorless gum: LCMS (M+H): 273.1. 1H NMR (CD3OD, 400 MHz): δ 9.58 (s, 1 H), 7.66–7.65 (m, 2 H), 7.59–7.55 (m, 1 H), 7.51–7.49 (m, 1 H), 4.39–4.26 (m, 2 H), 4.16 (m, 1 H), 3.31–3.28 (m, 2 H), 2.36–2.33 (m, 1 H), 1.98–1.87 (m, 3 H).

Provenance & Evidence