4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic Acid

Participants

Reaction Steps

The title compound was prepared according to the procedure in Example 4 using [2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (0.516 g, 1.14 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.540 g, 2.28 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 15 & 25% EtOAc/hexane step gradient gave 0.509 g (68%) of the tide compound as a brown solid, mp 72-82° C. 1H NMR (DMSO-d6) δ 1.25-1.34 (m, 2H), 1.50-1.55 (m, 2H), 1.62-1.74 (m, 4H), 1.77 (s, 3H), 2.15 (s, 3H), 2.95 (quintet, 1H), 3.88 (s, 2H), 7.10-7.15 (m, 2H), 7.20 (d, 1H), 7.27 (t, 1H), 7.35-7.37 (m, 2H), 7.48-7.58 (m, 3H), 7.96 (dd, 1H). IR (KBr) 3400, 2950, 1690, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 651 (M−H). Anal. Calcd. for C32H29BrO8S.0.4H2O: C, 58.17; H, 4.55; N, 0.00. Found: C, 58.20; H, 4.55; N, 0.03.

Provenance & Evidence