HCID 70113844, compound → HCID 178525229, compound

Participants

Reaction Steps

(S)-benzyl 2-(1-(2-(biphenyl-4-yl)-1-(1-(2-cyanoethyl)-1H-tetrazol-5-yl)ethylcarbamoyl)cyclopentyl)acetate (39 mg, 0.069 mmol) in MeOH (6 mL) was hydrogenated in H-Cube (Cartridge; 10% Pd/C) at room temperature for 0.5 hour. The reaction mixture was concentrated in vacuo. This was treated with 2M NaOH aqueous solution (1 mL) and MeOH (1 mL) and stirred for 0.5 hour. The reaction mixture was acidified with 1M HCl and the mixture was purified by reverse phase HPLC (column; Sunfire C-18, eluent; 0.1% TFA-H2O/CH3CN) to give {1-[(S)-2-biphenyl-4-yl-1-(1H-tetrazol-5-yl)-ethylcarbamoyl]-cyclopentyl}-acetic acid (2.5 mg). LCMS (condition C): 420 (M+1); retention time=1.70 min. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.36-1.54 (m, 6H), 1.87-1.98 (m, 2H), 2.59 (s, 3H), 2.59 (s, 2H), 3.22-3.66 (m, 2H), 5.39-5.48 (m, 1H), 7.29-7.37 (m, 3H), 7.44 (t, J=8.08 Hz, 2H), 7.55 (t, J=8.34 Hz, 2H), 7.59-7.64 (m, 2H), 8.17 (d, J=8.08 Hz, 1H); HRMS (ES+) m/z for C23H25N5O3 [M+H]+ calcd 419.2. found 419.2

Provenance & Evidence