Hydrochloric Acid → HCID 12052451, compound

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)

1. customthe solvents were removed under reduced pressure
2. customThe residue was dried under high vacuum for 18 hours
3. stirringthe mixture was stirred for 1 h
4. customThe solid was removed by filtration
5. customthe filtrate solvent was removed under reduced pressure
6. customto give an oil
7. customThis material was purified
8. customThe first eluting peak was collected
9. customafter removal of the solvents under reduced pressure
10. customdrying under high vacuum for 18 h

ORD record

ord-aacadd6612464da286405651663ebeeb

Source dataset

uspto-grants-2003_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06528503B2