Réaction #42281

Équation de réaction

Lithium hydroxide monohydrate

methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate

→

title compound

3-[(Dipropylamino)carbonyl]-5-ethylbenzoic acid

Solvants

THF methanol water

water

hydrochloric acid

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONis added
2. 2
   ExtractionThe aqueous mixture is extracted with ethyl acetate
3. 3
   AutreThe organic phase is separated
4. 4
   Lavagewashed with saline
5. 5
   Séchagedried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated

Mode opératoire

Lithium hydroxide monohydrate (0.0680 g, 1.6 mmol) is added to a mixture of methyl 3-[(dipropylamino)carbonyl]-5-ethylbenzoate (PREPARATION 20, 0.450 g, 1.6 mmol) in a mixture of THF/methanol/water (2/1/1, 8 mL). The mixture is stirred at 20-25 degrees C. for 3 hours. The mixture is then diluted with water (20 mL) and hydrochloric acid (1 N) is added to bring the pH to less than 3. The aqueous mixture is extracted with ethyl acetate. The organic phase is separated and washed with saline, dried over anhydrous magnesium sulfate, filtered and concentrated to give the title compound, MS (ESI+) for C16H23NO3 m/z (M+H)+=278.2.

Source