Methanol → HCID 69906473, compound

Participants

Reaction Steps

Trifluoroacetic acid (5 mL) is added to a solution of (±)-t-butyl (2R*,3R*)-2-hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoate (3.1 g, 6.7 mmol) in CH2Cl2 (20 mL). The reaction is monitored by TLC analysis (5% MeOH in CH2Cl2) and before all of the ester is consumed the reaction is concentrated and azeotroped with CHCl3 (3×15 mL). The crude product is purified by column chromatography (silica, 5% MeOH in CH2Cl2) to yield pure (±)-(2R*, 3R*)-2-Hydroxymethyl-3-(4-methoxybenzenesulfonyl)-7-phenylheptanoic acid (1.4 g, 51%): 1H NMR (300 MHz, CDCl3) δ 7.78 (d, J=7.0 Hz, 2H), 7.25-7.11 (m, 3H), 7.07-6.93 (m, 4H), 6.5-5.7 (bs, 1H), 4.34-4.26 (bm, 1H), 3.95-3.89 (bm, 1H), 3.82 (s, 3H), 3.81-3.69 (bm, 1H), 3.13-3.06 (bm, 1H), 2.46-2.37 (bm, 2H), 1.75-1.67 (bm, 2H), 1.48-1.30 (bm, 3H), 1.22-1.09 (bm, 1H); MS (FAB) m/e 406 (M+H)+.

Provenance & Evidence