反应详情

A suspension of methyl 6-[bis(methylsulfonyl)amino]-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxylate (2.88 g, 5.98 mmol) in ethanol (50 mL) and water (25 mL) was treated with potassium hydroxide (6.71 g, 120 mmol) and heated at reflux for 1 hour (the suspension went into solution upon heating). The reaction was concentrated under vacuum, water (100 mL) was added and the solution acidified with 2M HCl (50 mL). The resulting precipitate was filtered, washed with 0.5 M HCl, then dissolved in methanol. This solution was evaporated to dryness and azeotroped twice with toluene to give 5-Cyclopropyl-2-(4-fluorophenyl)-6-[(methylsulfonyl)amino]-1-benzofuran-3-carboxylic acid. LCMS (m/z, ES+)=390 (M+H+).

1. temperatureheated
2. temperatureat reflux for 1 hour (the suspension
3. temperatureupon heating)
4. concentrationThe reaction was concentrated under vacuum, water (100 mL)
5. additionwas added
6. filtrationThe resulting precipitate was filtered
7. washwashed with 0.5 M HCl
8. dissolutiondissolved in methanol
9. customThis solution was evaporated to dryness
10. customazeotroped twice with toluene