Hydrochloric Acid → HCID 12052454, compound

Participants

Reaction Steps

To a stirred solution of methyl 2-hydroxy-3-cyclopropylbutanoate (0.62 g, 3.9 mmol) in MeOH (10 mL) was added aqueous NaOH (1.0 mL of a 5.5 M solution, 5.5 mmol). The mixture was stirred at ambient temperature for 18 h. The mixture was brought to pH 2 by the addition of 6 N aqueous HCl and solvents were removed under reduced pressure. The residue was dried under high vacuum for several hours. The residue was suspended in dichloromethane (15 mL) and stirred for 1 h. The solid was removed by filtration and the filtrate solvent was removed under reduced pressure. The residue was purified on a Chiralpak AD column using 90:10:0.1 hexanes:2-propanol:TFA as eluant. Fractions containing the first-eluting peak were pooled and the solvents were removed under reduced pressure to give 2(R)-hydroxy-3(S)-cyclopropylbutanoic acid as a white solid. HPLC RT=1.98 min (Method A); 1H NMR 400 MHz, CDCl3, 4.36 ppm (d, J=2.9 Hz, 1H), 1.18 ppm (m, 1H), 1.00 ppm (d, J=7 Hz, 3H), 0.86 ppm (m, 1H), 0.54 ppm (m, 2H), 0.23 ppm (m, 1H), 0.18 ppm (m, 1H)

Provenance & Evidence