Hydrochloric Acid → (2S,3R)-N-Benzyl-2,3-dihydroxybutanamide

Participants

Reaction Steps

A flask was charged with 4.23 g (17.0 mmol) (4S,5R)-2,2,5-trimethyl-[1,3]dioxolane-4-carboxylic acid benzylamide, 30 mL acetonitrile, and 17 mL 0.5 M aqueous hydrochloric acid solution. This mixture was stirred overnight at room temperature. The solution was made neutral by the addition of 1 M aqueous sodium hydroxide solution. The solvent was removed under reduced pressure, and the crude residue was dried in a vacuum oven. The dry, crude material was purified by column chromatography (20:1 dichloromethane/methanol) to give 3.03 g (85%) of the title compound as a white solid. MS (APCI) (m+1)/z 210.1.

Provenance & Evidence