Methyl chloroformate → (2R)-2-(methoxycarbonylamino)propanoic Acid

To a solution of D-alanine (5 g, 56.1 mmol) in 1 N NaOH (152 mL, 152 mmol) at 0° C. is added a solution of MeOC(O)Cl (6.5 ml., 84.2 mmol) in diethyl ether (30 mL). The mixture is stirred in ice bath for 3 hours and then adjusted to pH 9 with 1 N NaOH. After stirring at room temperature for 1 hour, the mixture is washed with ether (3×50 mL), acidified to pH ˜2 with 5 N HCl, extracted with EtOAc (5×50 mL). The organic extract is washed with water, brine, and then dried (MgSO4). The solvent is removed to yield compound cxxxiv, N-methoxycarbonyl-D-alanine, as colorless oil (6.48 g, 79%).

1. stirringAfter stirring at room temperature for 1 hour
2. washthe mixture is washed with ether (3×50 mL)
3. extractionextracted with EtOAc (5×50 mL)
4. extractionThe organic extract
5. washis washed with water, brine
6. dry with materialdried (MgSO4)
7. customThe solvent is removed

ORD record

ord-596975076ab844bb954694cb13499115

Source dataset

uspto-grants-2012_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08252923B2