Methyl 2-(benzylamino)-2-phenylacetate → (Benzylamino)Phenylacetic Acid
Reaktionsgleichung
[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([O:12]C)=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>C1COCC1.[OH-].[Na+]>[CH2:1]([NH:8][CH:9]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:10]([OH:12])=[O:11])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1Komponenten
4
Edukt 1
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Versuchsvorschrift
A solution of methyl 2-(benzylamino)-2-phenylacetate (1.00 g, 3.90 mmol) in THF (90 mL) and 1N NaOH (10 mL) is stirred at room temperature overnight (LC-MS monitoring: complete conversion). The solvent is removed under reduced pressure and the crude is portioned between EtOAc and water. The aqueous phase is acidified with conc. HCl (pH about 3) and then extracted with EtOAc (three times). The organic phase is dried over Na2SO4, filtered and evaporated to dryness to give the title compound as a white solid (940 mg, quantitative yield), which is used in the next step without any further purification.