反应 #164303

反应方程式

HCl

LiOH

(R/S)-Ethyl 2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate

LiOH

→

(R/S)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid

收率 95.0%

溶剂

MeOH

THF

反应条件

后处理

1. 1
   workup.STIRRINGAfter stirring for 15 min
2. 2
   浓缩The reaction mixture was concentrated
3. 3
   workup.ADDITIONEtOAc was added
4. 4
   洗涤The EtOAc was washed with brine
5. 5
   其他The organic layer was dried
6. 6
   过滤filtered
7. 7
   浓缩concentrated

实验过程

(R/S)-Ethyl 2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetate (Int-VIII, 380 mg, 0.83 mmol) was dissolved in THF (5.00 mL) and MeOH (5 mL). Then, 1N LiOH (0.83 mL, 0.83 mmol) was added. It was stirred for 20 min and additional 1N LiOH (0.83 mL, 0.83 mmol) was added. After stirring for 15 min, the solution was neutralized by 1N HCl to pH=5. The reaction mixture was concentrated and then EtOAc was added. The EtOAc was washed with brine. The organic layer was dried, filtered and concentrated to give (R/S)-2-hydroxy-2-(4-(5-(5-phenyl-4-(trifluoromethyl)isoxazol-3-yl)-1,2,4-oxadiazol-3-yl)phenyl)acetic acid (Int-IX, 376 mg, 0.785 mmol, 95% yield): LCMS=432.1 [M+H]+; 1H NMR (400 MHz, methanol-d4) δ ppm 8.02-8.20 (2 H, m), 7.49-7.79 (7 H, m), 5.27 (1 H, s).

来源