反応 #160355

反応方程式

5-(3-Fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester

H2O

LiOH

→

5-(3-Fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid

収率 83.0%

溶媒

dioxane

反応条件

後処理

1. 1
   その他solvents were removed
2. 2
   その他partitioned between 10 ml of H2O
3. 3
   その他The organic layer was separated
4. 4
   洗浄the aqueous phase was washed twice with ethyl acetate (2×10 mL)
5. 5
   乾燥The combined ethyl acetate layer was dried (Na2SO4)
6. 6
   濃縮concentrated
7. 7
   その他the residue was purified by preparative chromatography (10% MeOH/CH2Cl2)

実験手順

5-(3-Fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid methyl ester (25 mg, 0.060 mmol) was dissolved in a 4:1 mixture of dioxane:H2O (0.8 mL) and then LiOH 1N (0.3 ml, 0.300 mmol) was added. After 3 hours of stirring at room temperature, solvents were removed and then partitioned between 10 ml of H2O acidified to pH 4 and 10 ml of EtOAc. The organic layer was separated and the aqueous phase was washed twice with ethyl acetate (2×10 mL). The combined ethyl acetate layer was dried (Na2SO4), concentrated and the residue was purified by preparative chromatography (10% MeOH/CH2Cl2) to obtain 20 mg (83%) of 5-(3-Fluoro-phenyl)-3-[isopropyl-(4-methyl-cyclohexanecarbonyl)-amino]-thiophene-2-carboxylic acid (Compound 5).

出典