Benzene → isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride

Reaction equation

[ClH:1].[NH2:2][C@@H:3]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:4]([OH:8])[C:5]([OH:7])=[O:6].[CH:13]1[CH:18]=CC=C[CH:14]=1>C(O)(C)C>[ClH:1].[NH2:2][C@@H:3]([CH2:9][CH:10]([CH3:12])[CH3:11])[CH:4]([OH:8])[C:5]([O:7][CH:13]([CH3:18])[CH3:14])=[O:6]

Participants

Procedure

Hydrogen chloride was passed into a solution of 4 g of (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoic acid in 50 ml of isopropyl alcohol with stirring under ice-cooling, and 100 ml of dry benzene was added to the mixture. The mixture was heated under reflux for 10 minutes while removing water formed during the reaction using a molecular sieve. The reaction mixture was concentrated under reduced pressure obtain 5.7 g of isopropyl (2RS,3S)-3-amino-2-hydroxy-5-methylhexanoate hydrochloride as a white powder.