Acetic Acid → HCID 57223582, compound

Participants

Reaction Steps

A 60% suspension of NaH in mineral oil (84 mg, 2.2 mmol) is carefully added to a solution of thiophenol (0.30 g, 2.7 mmol) in THF (10 mL) at 0° C. The mixture is allowed to warm to ambient temperature and is transferred to a solution of (±)-3-(R*)-[1-(R*)-(4-methoxybenzenesulfonyl)-5-phenylpentyl]-oxetan-2-one (0.63 g, 1.6 mmol) in THF (10 mL). The reaction is stirred 14 hours and then acidified with acetic acid. The crude mixture is azeotroped with methanol (2×50 mL) and purified by column chromatography using gradient elution (silica, 1 to 3% MeOH in CH2Cl2) to yield pure (±)-(2R*,3S*)-3-(4-methoxybenzenesulfonyl)-7-phenyl-2-(phenylsulfanylmethyl)heptanoic acid (0.64 g, 82%): m.p. 133-135; 1H NMR (300 MHz, CDCl3) δ 7.75 (d, J=8.6 Hz, 2H), 7.30-7.17 (m, 8H), 7.06 (d, J=7.3 Hz, 2H), 6.93 (d, J=8.6 Hz, 2H), 3.84 (s, 3H), 3.63 (bs, 1H), 3.52 (dd, J=14.2, 7.7 Hz, 1H), 3.14 (dd, J=14.2, 5.2 Hz, 1H), 2.98 (bs, 1H), 2.43 (t, J=7.4 Hz, 2H), 1.95-1.83 (m, 1H), 1.78-1.62 (m, 1H), 1.50-1.34 (m, 2H), 1.28-1.07 (m, 2H); MS (FAB) m/e 489 (M+); Anal. (C27H30O5S2) C, H, N.

Provenance & Evidence