Sodium Hydroxide → {4-[4-(2-Nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid

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Reaction Conditions

Reaction Steps

A mixture of {4-[4-(2-nitro-4-trifluoromethanesulfonyl-phenoxy)-benzenesulfonyl]-phenoxy}-acetic acid ethyl ester [Example 17, 61 mg, 0.1 mmol] in isopropanol (3.1 mL) and tetrahydrofuran (0.6 mL) was heated to reflux to dissolve all the solids. The mixture was cooled to 35° C. followed by addition of 1M NaOH solution (0.21 mL). It was then stirred at 35° C. for 2 hours. The reaction was concentrated, acidified with 1M HCl and extracted with ethyl acetate. The organic extracts were dried and concentrated to give the title compound. 1H NMR (300 MHz, DMSO-d6) δ 12.2 (br s, 1H, COOH), 10.57 (s, 1H), 8.36 (d, J=2.6 Hz, 1H), 7.79 (m, 1H), 7.78 (d, J=9.0 Hz, 2H), 7.72 (d, J=8.8 Hz, 2H), 7.06 (d, J=9.0 Hz, 2H), 7.01 (d, J=9.3 Hz, 1H), 6.89 (d, J=8.8 Hz, 2H), 4.77 (s, 2H).

Provenance & Evidence