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

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Reaction Steps

The title compound was prepared according to the procedure in Example 22 using 4-[4-(2-benzyl-4,5-dimethyl-thiophene-3-carbonyl)-2-cyclopentyl-phenoxysulfonyl]-2-hydroxy-benzoic acid (0.233 g, 0.394 mmol), magnesium iodide (0.110 g, 0.394 mmol) and acetic anhydride (3.3 mL) in ether. Purification on 2% H3PO4/MeOH treated silica gel, eluting with 18% EtOAc/pet ether followed by a second chromatography on 2% H3PO4/MeOH treated silica gel, eluting with 5% CH3CN/CH2Cl2 gave 0.128 g (51%) of the title compound as a white solid, mp 94-96° C. 1H NMR (DMSO-d6) δ 1.24-1.33 (m, 2H), 1.52-1.57 (m, 2H), 1.61-1.76 (m, 4H), 1.79 (s, 3H), 2.23 (s, 3H), 2.26 (s, 3H), 2.94 (quintet, 1H), 3.85 (s, 2H), 6.99-7.01 (m, 2H), 7.13 (m, 4H), 7.52 (dd, 1H), 7.59 (d, 1H), 7.84 (d, 1H), 7.90 (dd, 1H), 8.14 (d, 1H), 13.8 (br s, 1H). mass spectrum (−ESI) m/z 631 (M−H). Anal. Calcd. for C34H32O8S20.2H2O: C, 64.17; H, 5.13; N, 0.00. Found: C, 64.06; H, 4.98; N, 0.04.

Provenance & Evidence