Reacción #47405

Ecuación de reacción

(S)-4-methyl-2-(2-oxo-4-o-tolyloxy-2,5-dihydro-pyrrol-1-yl)-pentanoic acid methyl ester

lithium hydroxide monohydrate

→

(S)-4-methyl-2-(2-oxo-4-o-tolyloxy-2,5-dihydro-pyrrol-1-yl)-pentanoic acid

Rendimiento 91.2%

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   Otrothe solvents evaporated
2. 2
   workup.DISSOLUTIONThe residue was dissolved in water
3. 3
   Lavadowashed with diethyl ether
4. 4
   Extracciónextracted with ethyl acetate
5. 5
   SecadoThe combined organic layers were dried over sodium sulfate
6. 6
   Concentraciónconcentrated

Procedimiento

To a solution containing (S)-4-methyl-2-(2-oxo-4-o-tolyloxy-2,5-dihydro-pyrrol-1-yl)-pentanoic acid methyl ester (1.50 g, 4.7 mmol) in tetrahydrofuran (30 mL) was treated with an aqueous solution of lithium hydroxide monohydrate (0.5N, 20 mL, 10.0 mmol). The mixture was stirred at 20° C. for 3 h, and the solvents evaporated. The residue was dissolved in water and washed with diethyl ether, and the diethyl ether layer discarded. The aqueous phase was acidified with dilute hydrochloric acid (pH <2), and extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate and concentrated to afford (S)-4-methyl-2-(2-oxo-4-o-tolyloxy-2,5-dihydro-pyrrol-1-yl)-pentanoic acid (1.30 g, 91%) as a tan solid.

Fuente