反应详情

Lithium hydroxide (60 mg, 2.51 mmol) in water (1 mL) was added dropwise to a stirring solution of methyl 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoate (3) (267 mg, 56%) (240 mg, 0.628 mmol) in THF (5 mL) and the resulting yellow solution was stirred for 5 days at RT. The solvent was evaporated in vacuo and dissolved in water (5 mL), then acidified with 2 M HCl. The resultant mixture was extracted with EtOAc. The organic layer was washed with water, dried over MgSO4 and filtered and pre-adsorbed on silica. Silica gel chromatography (40 g, 0-10% IPA in DCM) provided 4-(3,5-dichloro-4-ethoxybenzamido)-2-methylbenzoic acid (AAA-019) (52 mg, 22%): m/z 366 (M−H)− (ES−). 1H NMR (400 MHz, DMSO-d6) δ: 12.66 (1H, s), 10.49 (1H, s), 8.08 (2H, s), 7.87 (1H, d), 7.71 (1H, dd), 7.68 (1H, d), 4.14 (2H, q), 2.54 (3H, s), 1.40 (2H, t).

1. customThe solvent was evaporated in vacuo
2. dissolutiondissolved in water (5 mL)
3. extractionThe resultant mixture was extracted with EtOAc
4. washThe organic layer was washed with water
5. dry with materialdried over MgSO4
6. filtrationfiltered and pre-adsorbed on silica