Methanol → 2-[[3,5-bis(trifluoromethyl)benzoyl]amino]-4-[3-[(E)-[4-(trifluoromethyl)phenyl]methylideneamino]oxypropoxy]benzoic acid

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Reaction Steps

This compound was produced using similar methods as those used in Step 6, example 28, starting with 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.22 g, 0.35 mmol), 1:1 methanol:tetrahydrofuran (10 mL) and 4N aqueous lithium hydroxide solution (0.26 mL). The crude material was triturated with hot hexanes and filtered. The product was then crystallized from hot chloroform (10 mL) by the addition of room temperature hexanes (100 mL), and allowing the mixture to sit for 2 hours to give 2-{[3,5-bis(trifluoromethyl)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid (0.055 g, 26%) as a white solid. mp=218-219° C. (dec). 1H NMR (500 MHz, DMSO-d6); δ 13.50 (bs, 1H), 12.72 (s, 1H), 8.49 (s, 2H), 8.44 (s, 1H), 8.38 (s, 1H), 8.31 (d, 1H), 7.99 (d, 1H), 7.80-7.71 (AA′BB′, 4H), 6.82 (dd, 1H), 4.34 (t, 2H), 4.22 (t, 2H), 2.18 (m, 2H). Mass spec (MW 622.44); (ES+) m/z 623.05, (ES−) m/z 621.50. Elemental analysis; Calculated for C27H19F9N2O5: C, 52.10; H, 3.08; N, 4.50. Found: C, 51.78; H, 3.03; N, 4.26.

Provenance & Evidence