Hydrochloric Acid → HCID 57695565, compound

Participants

Reaction Conditions

Reaction Steps

2′,4′-Bis-benzyloxy-5′-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-biphenyl-3-carboxylic acid methyl ester (1 mmol) was dissolved in mixture of THF (5 ml) and water (5 ml). LiOH (72 mg, 3 mmol) was added, and the resulting mixture was stirred at 80° C. overnight. After the reaction was complete, the reaction was cooled to r.t., acidified with 1M HCl to pH=1. After extraction with ether (25 ml×3), the combined organics were washed with water (25 ml) and saturated brine (25 ml) and dried over Na2SO4. After filtration and concentration, 2′,4′-bis-benzyloxy-5′-[1-(3-methoxy-propyl)-1H-tetrazol-5-yl]-biphenyl-3-carboxylic acid was obtained as white solid in quantitative yield. M.p.: 59-63° C.; 400 MHz 1H NMR (DMSO-d6) δ: 12.98 (br s, 1H), 8.18 (t, J=1.6 Hz, 1H), 7.89 (d, J=7.6 Hz, 1H), 7.78 (d, J=7.6 Hz, 1H), 7.54-7.28 (m, 13H), 5.32 (s, 2H), 5.31 (s, 2H), 4.27 (t, J=7.2 Hz, 2H), 3.18 (t, J=6.0 Hz, 2H), 3.06 (s, 3H), 1.93 (pent, J=6.8 Hz, 2H); LCMS: 551 [M+H].

Provenance & Evidence