Hydrochloric Acid → HCID 12052451, compound

Participants

Reaction Steps

To a stirred solution of methyl 2-hydroxy-3-(1-methyl-cyclopropyl)propanoate (1.4 g, 8.1 mmol) in EtOH (10 mL) was added aqueous NaOH (2.2 mL of a 5.0 M solution, 11 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 the solvents were removed under reduced pressure. The residue was dried under high vacuum for 18 hours. The residue was suspended in dichloromethane (15 mL) and the mixture was stirred for 1 h. The solid was removed by filtration and the filtrate solvent was removed under reduced pressure to give an oil. This material was purified using a Chiralpak AD column using 95:5:0.1 hexanes:2-propanol:TFA as the eluant. The first eluting peak was collected and after removal of the solvents under reduced pressure and drying under high vacuum for 18 h, 2(R)-hydroxy-3-(1-methyl-cyclopropyl)propanoic acid was obtained a white solid. HPLC RT=2.00 min (Method A)

Provenance & Evidence