1-Fluoro-2-nitrobenzene → N-(2-nitrophenyl)-O-benzyl-D-serine methyl ester

Temperature

0 °C

To a solution of O-benzyl-D-serine methyl ester (3,13 g, 14.96 mmol) in MeOH, was added 2-fluoronitrobenzene (1.6 mL, 15.08 mmol) and NaHCO3 (1.3 g, 15.48 mmol), and the resulting solution was brought to a reflux for approximately one day. The reaction mixture was then cooled, filtered, concentrated and chased with benzene (4×50 ml). The residue was re-dissolved in EtOAc, cooled to 0° C. and HCl gas was bubbled into the resulting solution until it reached a pH of ˜4. The reaction mixture was allowed to warm to room temperature and stirred for 5 hours. Upon completion, the reaction mixture was washed with saturated NaHCO3 (3×50 mL), dried over sodium sulfate, filtered and concentrated under reduced pressure. The crude product was subjected to silica gel chromatography eluting with 8%-30% EtOAc in Hexanes to give 1.09 g (3.30 mmol) of N-(2-nitrophenyl)-O-benzyl-D-serine methyl ester.

1. temperaturea reflux for approximately one day
2. temperatureThe reaction mixture was then cooled
3. filtrationfiltered
4. concentrationconcentrated
5. dissolutionThe residue was re-dissolved in EtOAc
6. customHCl gas was bubbled into the resulting solution until it
7. temperatureto warm to room temperature
8. washUpon completion, the reaction mixture was washed with saturated NaHCO3 (3×50 mL)
9. dry with materialdried over sodium sulfate
10. filtrationfiltered
11. concentrationconcentrated under reduced pressure
12. washeluting with 8%-30% EtOAc in Hexanes

ORD record

ord-e734164918ed4093bf55135a54b61b68

Source dataset

uspto-grants-2005_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06908921B2