(2R*,3S*)-2-(tert-butoxy-carbonylamino)-3-hydroxy-4,4-dimethyl-pentanoate → (2R,3S)-2-Amino-3-Hydroxy-4,4-Dimethylpentanoic Acid

Participants

Reaction Conditions

Reaction Steps

In a round-bottomed flask, the diastereomeric mixture containing (2R*,3R*)- and (2R*,3S*)-2-(tert-butoxy-carbonylamino)-3-hydroxy-4,4-dimethyl-pentanoate (0.4 g, 1.38 mmol) was dissolved in a 6.0 M HCl solution (30 mL). The resulting solution was divided into two equal aliquots and stirred at 130° C. for 1 h. All portions were joined and the reaction mixture extracted with Et2O (3×20 mL). The aqueous phase was concentrated under reduced pressure giving a yellowish solid crude product, as a diastereoisomeric mixture (anti:syn=9:1), which was used without further purification in the following step. MS (ESI) m/z: 162 [M−H]+; (ESI) m/z: 160 [M−H]−.

Provenance & Evidence