4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[2-(4-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-(4-bromo-benzyl)-4,5-dimethyl-furan-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (0.203 g, 0.448 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (0.319 g, 1.34 mmol). Purification on Dynamax C18 (85% CH3CN/H2O) gave 0.221 g (49%) of the title compound as a brown solid, mp 188-192° C. 1H NMR (DMSO-d6) δ 1.26-1.32 (m, 2H), 1.49-1.57 (m, 2H), 1.64-1.74 (m, 4H), 1.77 (s, 3H), 2.18 (s, 3H), 2.96 (quintet, 1H), 3,79 (s, 2H), 6.96 (d, 2H), 7.23 (d, 1H), 7.36-7.43 (m, 4H), 7.53-7.56 (m, 2H), 8.00 (d, 1H). IR (KBr) 3400, 2950, 1690, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 651 (M−H). Anal. Calcd. for C32H29BrO8 S: C, 58.81; H, 4.47; N, 0.00. Found: C, 58.45; H, 4.54; N, 0.07.

Provenance & Evidence