[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:23]2[CH:27]=[N:26][N:25]=[N:24]2)=[C:6]([CH:22]=1)[CH2:7][NH:8][C:9]([C@@H:11]([NH:14]C(=O)OC(C)(C)C)[CH2:12][CH3:13])=[O:10].Cl.CO.Cl.O1CCOCC1>CCOC(C)=O.O1CCOCC1>[NH2:14][C@@H:11]([CH2:12][CH3:13])[C:9]([NH:8][CH2:7][C:6]1[CH:22]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=1[N:23]1[CH:27]=[N:26][N:25]=[N:24]1)=[O:10]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).
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