4-(Chlorosulfonyl)-2-hydroxybenzoic acid → 4-{4-[2-(4-Bromo-benzyl)-4,5-dimethyl-thiophene-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-bromobenzyl)-4,5-dimethyl-thiophen-3-yl]-(3-cyclopentyl-4-hydroxy-phenyl)-methanone (1.01 g, 2.14 mmol) and 4-chlorosulphonyl-2-hydroxybenzoic acid (1.01 g, 4.29 mmol). Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 15 & 25% EtOAc/hexane step gradient followed by crystallization from ether/pet ether gave 0.549 g (38%) of the title compound as a tan solid, mp 165-170° C. 1H NMR (DMSO-d6) δ1.22-1.32 (m, 2H), 1.46-1.58 (m, 2H), 1.61-1.76 (m, 4H), 1.78 (s, 3H), 2.26 (s, 3H), 2.97 (quintet, 1H), 3.84 (s, 2H), 6.94 (d, 2H), 7.23 (d, 1H), 7.34-7.40 (m, 4H), 7.50 (dd, 1H), 7.53 (d, 1H), 8.00 (d, 1H). IR (KBr) 3400, 2950, 1680, 1480, 1390 and 1190 cm−1. mass spectrum (−ESI) m/z 667 (M−H). Anal. Calcd. for C32H29BrO7S2: C, 57.40; H, 4.37; N, 0.00. Found: C, 57.47; H, 4.24; N, 0.08.

Provenance & Evidence