Water → [5-Methoxy-2-methyl-4-(4'-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid

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Reaction Steps

Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid methyl ester (compound 51A) Example 4 (0.5 g, 1.0 mmol) was dissolved in 25 ml dichloromethane followed by the addition of 2-benzenesulfonyl-3-phenyl-oxaziridine (0.274, 1.04 mmol). The reaction was stirred 1 h. 10 ml water was added, the layers were separated, and dichloromethane solution was dried over anhydrous sodium sulfate, decanted, and concentrated. The product was recrystallized from ethyl acetate to give the title product. MS m/z 493 (M+1). Step 2. Preparation of [5-Methoxy-2-methyl-4-(4′-trifluoromethyl-biphenyl-4-ylmethanesulfinyl)-phenoxy]-acetic acid (compound 51) The title compound was prepared in the manner analogous to Example 1 using 51A. 400 MHz 1H NMR (DMSO-d6) δ 7.83 (d, 2H, J=8.78 Hz), 7.76 (d, 2H, J=8.30 Hz), 7.59 (d, 2H, J=8.30 Hz), 7.11 (d, 2H, J=8.30 Hz), 7.02 (s, 1H), 6.64 (s, 1H), 4.79 (s, 2H), 4.20 (d, 1H, J=12.7 Hz), 3.91 (d, 1H, J=12.4 Hz), 3.76 (s, 3H), 2.03 (s, 3H). MS m/z 479 (M+1).

Provenance & Evidence