L-Valine → 2-((Methoxycarbonyl)amino)-3-methylbutanoic acid

Temperature

0 °C

To a solution of L-valine, d8 (Cambridge Isotope Laboratories, 0.4949 g) in 1N sodium hydroxide (3.95 mL) was added sodium carbonate (0.419 g). The solution was cooled to 0° C. and methyl chloroformate (0.289 mL) was added dropwise over 30 minutes and reaction mixture was stirred for 3 h at 0° C. Reaction mixture was washed with ethyl ether (3×15 mL) and aqueous layer was acidified to pH=1 with concentrated HCl. Aqueous layer was extracted dichloromethane (3×15 mL) and organic layers were dried (MgSO4) and concentrated to give 2-Methoxycarbonylamino-3-methyl-butyric acid, d8 as a white solid (0.5681 g). LCMS-ESI−: calc'd for C7H5D8NO4: 184.2 (M+H+). Found: 184.0 (M+H+).

1. customreaction mixture
2. customReaction mixture
3. washwas washed with ethyl ether (3×15 mL) and aqueous layer
4. extractionAqueous layer was extracted dichloromethane (3×15 mL) and organic layers
5. dry with materialwere dried (MgSO4)
6. concentrationconcentrated

ORD record

ord-b73c04a2233042ab89d50b3d6deefbfd

Source dataset

uspto-grants-2014_09

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08822430B2