Reaction #47570

Reaction equation

(S)-3-cyclohexyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester

lithium hydroxide

→

(S)-3-cyclohexyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid

Yield 67.5%

Solvents

tetrahydrofuran water

Conditions

Workup

1. 1
   ConcentrationAfter this time, the mixture was concentrated
2. 2
   workup.ADDITIONthe reaction mixture was diluted with water
3. 3
   OtherThe reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation
4. 4
   OtherThe precipitate was removed by filtration
5. 5
   Washwashed with cold water
6. 6
   Otherdried in vacuo

Procedure

To a stirred solution of (S)-3-cyclohexyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid methyl ester (490 mg, 1.36 mmol) in tetrahydrofuran-water (3:1, 10 mL) was added lithium hydroxide (172 mg, 4.1 mmol). The reaction mixture was stirred at 23° C. for 2 h. After this time, the mixture was concentrated and the reaction mixture was diluted with water. The reaction mixture was acidified with 2N hydrochloric acid, during which time precipitation occurred. The precipitate was removed by filtration, washed with cold water and dried in vacuo to obtain (S)-3-cyclohexyl-2-[4-(6-methyl-pyridin-3-yloxy)-2-oxo-2,5-dihydro-pyrrol-1-yl]-propionic acid (316 mg, 67%) as a brown solid.

Source