Sulfuric Acid → (S)-3-Phenylamino-butyramide

Participants

Reaction Steps

To a solution of (S)-3-phenylamino-butyronitrile (6.06 g, 0.0378 mol) in toluene (150 mL) was added a cooled solution of conc. sulfuric acid in H2O (20.12 mL H2SO4/3 mL)—(The ratio of toluene to acid/H2O is very important and should be followed strictly). Stir the biphasic mixture at room temperature for 0.5 h and warm to 35° C. and stir for 22 h. The reaction was cooled to room temperature and quenched with 13 g of Na2CO3 in water (add slowly some foaming). Separate the organic and extract 2×EtOAc. Combine all the organics and wash the organics with brine, dry over MgSO4, filter and concentrate to give the desired product in 2.11 g (90%)

Provenance & Evidence