Acetic Anhydride → HCID 10282528, compound

Participants

Reaction Steps

A stirred solution containing 4-[4-(2-benzyl-4,5-dimethyl-furan-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.235 g, 0.409 mmol), acetic anhydride (3.3 mL) and magnesium iodide (0.113 g, 0.409 mmol) in ether (8 mL) was refluxed for 0.5 h. The reaction was allowed to cool to ambient temperature, quenched with H2O (100 mL), extracted with ether and concentrated. The mixed anhydride/product was dissolved in THF (6 mL), treated with H2O (6 mL) and refluxed for 0.5 h. The reaction was allowed to cool to ambient temperature, quenched with H2O (100 mL), extracted with ether and concentrated. Purification on 2% H3PO4/MeOH treated silica gel, eluting with a 18 & 25% EtOAc/pet ether step gradient followed by crystallization from acetone/hexane gave 0.201 g (80%) of the title compound as an off white solid, mp 55-90° C. 1H NMR (DMSO-d6) δ1.23-1.32 (m, 2 H), 1.50-1.53 (m, 2 H), 1.64-1.72 (m, 4 H), 1.76 (s, 3 H), 2.17 (s, 3 H), 2.23 (s, 3 H), 2.92 (quintet, 1 H), 3.79 (s, 2 H), 6.98-7.00 (m, 2 H), 7.15-7.23 (m, 4 H), 7.53 (dd, 1 H), 7.58 (d, 1 H), 7.84 (d, 1 H), 7.88 (dd, 1 H), 8.12 (d, 1 H) 13.7 (br s, 1 H). mass spectrum (−ESI) m/z 615 (M−H). Anal. Calcd. for C34H32O9S .0.5H2O: C, 65.27; H, 5.32; N, 0.00. Found: C, 65.33; H, 5.30; N, 0.03.

Provenance & Evidence