Hydrochloric Acid → HCID 9857135, compound

Participants

Reaction Steps

To a solution of 4-acetylthiomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid, dimethyl ester (0.27 g, 0.75 mmol) in deoxygenated THF was added a degassed solution of sodium hydroxide (0.12 g, 3.0 mmol) in H2O (5 mL) at room temperature. After 24 hours, additional solution of sodium hydroxide (0.09 g) in H2O (2 mL) was added to the reaction mixture and the mixture was stirred for 24 hours. The mixture was acidified with 10% HCl and extracted with EtOAc. The extract was dried over MgSO4 and concentrated. The crude material was purified by column chromatography with (9:1 dichloromethane/EtOAc with 1% acetic acid) to afford 4-mercaptomethyl-[1,1′-biphenyl]-2,3′-dicarboxylic acid (0.20 g, 92%) as a white solid: 1H NMR (DMSO-d6) δ 3.10 (t, J=8.03 Hz, 1H), 3.89 (d, J=8.03 Hz, 2H), 7.43 (d, J=7.53 Hz, 1H), 7.58-7.65 (m, 3H), 7.83 (d, J=2.01 Hz, 1H), 7.92 (s, 1H), 7.97-8.00 (m, 1H). Elemental analysis calculated for C15H12O4S.0.5 AcOH: C, 60.37; H, 4.43; O, 25.13; S, 10.07. Found: C, 60.28; H, 4.45; S, 10.15.

Provenance & Evidence