1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → [5-(1'-{[2,6-Dimethoxybiphenyl-4-yl]carbonyl}-4-oxospiro[chroman-2,4'-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate

Participants

Reaction Conditions

Reaction Steps

Triethylamine (0.23 mL) and water (2.0 mL) were added to a DMF (6.0 mL) solution of 2,6-dimethoxy-biphenyl-4-carboxylic acid (258 mg), [5-(4-oxospiro[chroman-2,4′-piperidin]-6-yl)-tetrazol-2-yl]methyl 2,2-dimethylpropanoate hydrochloride (500 mg), WSC (288 mg) and HOBT (202 mg), and stirred at 90° C. for 1 hour. Water was added to it at room temperature, and a white precipitate was thus obtained. This was dried under reduced pressure to obtain the title compound as a colorless solid. 1H-NMR (400 MHz, DMSO-d6) δ: 8.40 (1H, d, J=2.2 Hz), 8.26 (1H, dd, J=8.8, 2.2 Hz), 7.38-7.18 (6H, m), 6.75 (2H, s), 6.64 (2H, s), 4.35-4.21 (1H, m), 3.68 (6H, s), 3.65-3.39 (2H, m), 3.29-3.25 (1H, m), 2.98 (2H, s), 2.14-1.92 (2H, m), 1.89-1.78 (2H, m), 1.14 (9H, s). MS [M+H]+=640.

Provenance & Evidence