Hydrochloric Acid → (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanoic acid

Participants

Reaction Conditions

Reaction Steps

To (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanenitrile (93.0 g; 0.301 mol) was added 12N hydrochloric acid (465 mL). The resulting mixture was heated to reflux (100° C.) for 3 hours, monitoring progress of the reaction by TLC analysis (ethyl acetate/hexane, 1:1). After TLC analysis indicated that the reaction was complete, the reaction mixture was cooled, and the pH was adjusted to 6-7 using 6N aqueous sodium hydroxide solution (930 mL). The product was extracted with two portions of dichloromethane (2×700 mL), and the combined organic phases were dried over sodium sulfate. After filtration the solvent was removed under reduced pressure, to give 95.0 g (96%) of (2S,3S)-3-(dibenzylamino)-2-hydroxyhexanoic acid as a solid.

Provenance & Evidence