反応 #57957

反応方程式

4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester

4-trifluoromethyl-benzaldehyde oxime

cesium carbonate

→

2-{[4-(trifluoromethoxy)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester

収率 78.0%

溶媒

acetone

反応条件

後処理

1. 1
   その他This compound was produced
2. 2
   その他The crude material was purified by flash chromatography through silica gel

実験手順

This compound was produced using similar methods as those used in Step 5, example 27, starting with 4-(3-bromo-propoxy)-2-(4-trifluoromethoxy-benzoylamino)-benzoic acid methyl ester (0.46 g, 0.97 mmol), 4-trifluoromethyl-benzaldehyde oxime (0.19 g, 1.01 mmol) and cesium carbonate (1.26 g, 3.86 mmol) in acetone (35 mL). The crude material was purified by flash chromatography through silica gel using diethyl ether/hexanes (0/100 gradient to 10/90) to give 2-{[4-(trifluoromethoxy)benzoyl]amino}-4-{3-[({(1E)-[4-(trifluoromethyl)phenyl]methylidene}amino)oxy]propoxy}benzoic acid methyl ester (0.44 g, 78%) as a white solid. 1H NMR (500 MHz, DMSO-d6); δ 11.92 (s, 1H), 8.38 (s, 1H), 8.32 (d, 1H), 8.05 (d, 2H), 7.97 (d, 1H), 7.80-7.21 (AA′BB′, 4H), 7.60 (d, 2H), 6.82 (dd, 1H), 4.34 (t, 2H), 4.21 (t, 2H), 3.87 (s, 3H), 2.18 (m, 2H).

出典