565460-54-0

Questions And Answer

• Synthesis

  To a solution of dimethyl D-aspartate (18 g, 111.7 mmol) in MeOH (500 mL) was added 2-flfluoronitrobenzene (17.33 g, 122.86 mmol) and NaHCO3 (9.38 g, 111.7 mmol). The reaction mixture was reflfluxed under N2 for approximately 2 days. The solvent was removed under reduced pressure, and the residue was azeotropically dried with benzene (2 × 100 mL). The crude material was then redissolved in MeOH (200 mL), cooled to 0 ºC, and the pH of the reaction mixture was adjusted to 4 with HCl(g). The reaction mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was taken up in EtOAc and washed with a saturated NaHCO3/10% Na2CO3 solution (9:1, 2 × 500 mL) and brine (300 mL). The organic layer was dried over sodium sulfate, fifiltered, and concentrated to give dimethyl (2R)-2-(2-nitrophenylamino)butanedioate (25.54 g, 81%).
  
  Reference: Su, D.-S.; Markowitz, M. K.; DiPardo, R. M.; Murphy, K. L.; Harrell, C. M.; O’Malley, S. S.; Ransom, R. W.; Chang, R. S. L.; Ha, S.; Hess, F. J.; Pettibone, D. J.; Mason, G. S.; Boyce, S.; Freidinger, R. M.; Bock, M. G. J. Am. Chem. Soc. 2003, 125, 7516–7517
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