Acetic Anhydride → 2-Acetoxy-4-{4-[2-(2-Bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-benzoic Acid

Participants

Reaction Steps

The title compound was prepared according to the procedure in Example 22 using 4-{4-[2-(2-bromo-benzyl)-4,5-dimethyl-furan-3-carbonyl]-2-cyclopentyl-phenoxysulfonyl}-2-hydroxy-benzoic acid (0.318 g, 0.487 mmol), magnesium iodide (0.132 g, 0.475 mmol) and acetic anhydride (3.8 mL) in ether. Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 30% EtOAc/pet ether gave 0.083 g (25%) of the title compound as a solid, mp 79° C. 1H NMR (DMSO-d6) δ 1.27-1.33 (m, 2H), 1.51-1.54 (m, 2H), 1.63-1.73 (m, 4H), 1.79 (s, 3H), 2.17 (s, 3H), 2.24 (s, 3H), 2.93 (quintet, 1H), 3.91 (s, 2H), 7.13-7.17 (m, 2H), 7.21 (d, 1H), 7.30 (dt, 1H), 7.51 (dd, 1H), 7.55 (dd, 1H), 7.60 (d, 1H), 7.85 (d, 1H), 7.90 (dd, 1H), 8.14 (d, 1H)13.8 (br s, 1H). mass spectrum (−ESI) m/z 693/695 (M−H). Anal. Calcd. for C34H31BrO9S: C, 58.71; H, 4.49; N, 0.00. Found: C, 58.04; H, 4.52; N, 0.04.

Provenance & Evidence