{4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5-yl]-acetic acid → {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-(2H-tetrazol-5-yl)-acetic acid

Participants

Reaction Steps

10% Pd/C (40 mg) is added to a stirred slurry of {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)--ethyl]-phenoxy}-[2-(1-methyl-1-phenyl-ethyl)-2H-tetrazol-5- yl]-acetic acid of Step D (0.045 g, 0.068 mmol) and HCO2K (0.034 g, 0.409 mmol) in EtOH (2 mL). The reaction mixture is heated to reflux under N2. After 5 h, the reaction mixture is cooled to RT and filtered to remove Pd/C. The filtrate is diluted with EtOAc, water and 10% HCl and the layers separated. The organic layer is washed with 10% HCl and brine, dried (MgSO4) and concentrated under reduced pressure to provide {4-[(2S)-2-benzoylamino-2-(4-phenyl-butylcarbamoyl)-ethyl]-phenoxy}-(2H-tetrazol-5-yl )-acetic acid (compound 18); 1H NMR (400 MHz, acetone-d6) δ7.82 (m, 3H), 7.45 (m, 4H), 7.19 (m, 7H), 6.99 (d, 2H), 6.36 (s, 1H), 4.81 (m, 1H), 3.21 (m, 3H), 3.05 (m, 1H) 2.58 (t, 2H), 1.59 (m, 2H), 1.48 (m, 2H); MS (ES+) m/z 543 (M+1); MS (ES−) m/z 541 (M−1).

Provenance & Evidence