Benzyl [(R)-4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-YL]carbamate → (3R)-3-Amino-N,N-dimethyl-4-(phenylsulfanyl)butanamide

Participants

Reaction Steps

A suspension of (R)-benzyl 4-(dimethylamino)-4-oxo-1-(phenylthio)butan-2-ylcarbamate (INTERMEDIATE 15, 40 g, 0.10 mol) in 40% HBr in acetic acid (100 ml) was stirred at room temperature for 16 hours and the reaction mixture became homogeneous during this time. The mixture was concentrated to dryness, diluted with water (200 ml) and AcOH (200 ml) and washed with diethyl ether (3×50 ml). The aqueous phase was brought to approximately pH 8-9 with solid Na2CO3 and was extracted with CH2Cl2 (5×) The combined organic phases were dried (MgSO4) and concentrated under reduced pressure to give the title product (15 g, 59%) that was used in the preparation of INTERMEDIATE 17 without further purification.

Provenance & Evidence