Reaction #47239

Reaction equation

(S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester

lithium hydroxide monohydrate

hydrochloric acid

→

(S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid

Yield 77.9%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   ExtractionThe mixture was extracted with ethyl acetate (2×30 mL)
2. 2
   DryingThe combined organic layers were dried over magnesium sulfate
3. 3
   Concentrationconcentrated

Procedure

To a solution containing (S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid methyl ester (1.82 g, 6.48 mmol) in tetrahydrofuran (15 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (8.4 mL, 1.0 M, 8.42 mmol). The mixture was stirred at 25° C. for 2 h then, acidified with 2N aqueous hydrochloric acid. The mixture was extracted with ethyl acetate (2×30 mL). The combined organic layers were dried over magnesium sulfate and concentrated to afford (S)-3-cyclohexyl-2-(4-methoxy-2-oxo-2,5-dihydro-pyrrol-1-yl)-propionic acid, (1.35 g, 75%) as a yellow solid.

Source