The title compound was prepared from N-(tert-butoxycarbonyl)-4-methyl]-D-leucine (32 mg, 0.13 mmol), N-[5-chloro-2-(1H-1,2,4-tetraazol-1-yl)benzyl]-L-prolinamide (Example 26, Step B, 50 mg, 0.21 mmol, 1.0 equiv), EDC (38 mg, 0.20 mmol, 1.5 equiv) and HOAt (9 mg, 0.07 mmol, 0.5 equiv) in DMF (1 mL) followed by deprotection in TFA-CH2Cl2 essentially according to the procedure described in Example 27, Step C. Purification by reverse phase chromatography [95:5 water (+0.1% TFA)/CH3CN (+0.1% TFA) to 50:50 water (+0.1% TFA)/CH3CN (+0.1% TFA)] followed by lyophilization of the fractions afforded the title compound as a white powder. 1H NMR (400 MHz, CDCl3): δ 9.18 (s, 1 H), 8.45 (br s, 2 H), 8.00 (t, J=5.2 Hz, 1 H), 7.73 (d, J=2.0 Hz, 1 H), 7.41 (dd, J=2.0, 8.4 Hz, 1 H), 7.19 (d, J=8.4 Hz, 1 H), 4.41–4.34 (m, 2 H), 4.25 (dd, J=4.8, 14.8 Hz, 1 H), 4.00–3.94 (m, 1 H), 3.89–3.85 (m, 1 H), 3.53–3.46 (m, 1 H), 2.25–2.22 (m, 1 H), 2.09–1.85 (m, 5 H), 1.00 (s, 9 H). HRMS (APCI) M+H: calculated for (C20H28N7O2Cl)+ 434.2066, found 434.2065.
