[NH2:1][CH:2]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[F:12])[C:3]([OH:5])=[O:4].[OH-].[Na+].Cl[C:16]([O:18][CH3:19])=[O:17].Cl>C1COCC1>[F:12][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=1[CH:2]([NH:1][C:16]([O:18][CH3:19])=[O:17])[C:3]([OH:5])=[O:4]Amino-(2-fluoro-phenyl)-acetic acid (0.5 g, 2.44 mmol) was dissolved in THF (7 mL) and cooled to 0° C. in an external ice/brine bath. Aqueous sodium hydroxide (12.5M, 0.47 mL, 5.856 mmol) and methyl chloroformate (0.23 mL, 2.948 mmol) were added at 0° C. Upon completion of the addition, the solution was removed from the ice bath and allowed to warm to room temperature, and stirred. After 18 hours, the crude reaction mixture was adjusted to pH 1 with 1N HCl and extracted twice with diethyl ether. The combined organic layers were washed with brine, dried with magnesium sulfate and concentrated to give (2-Fluoro-phenyl)-methoxycarbonylamino-acetic acid as an off-white solid. LCMS-ESI+: calc'd for C10H10FNO4: 227.06 (M+); Found: 228.17 (M+H+).
Loading…
