反应详情

(S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (5.5 g, 26.8 mmol, Eq: 1.00) was dissolved in DMF (90 mL) at 0° C. and NaH (60% in mineral oil, 2.57 g, 64.3 mmol, Eq: 2.4) was added in small portions The mixture was stirred for 30 min. and 2-fluoro-4-methyl-1-nitrobenzene (4.16 g, 26.8 mmol, Eq: 1.00) in DMF (10 mL) was added dropwise. The resulting mixture was stirred for 60 min., diluted with 1.0 M KHSO4 and extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over Na2SO4 and concentrated. The residue was purified by silica gel chromatography to afford (S)-2-(tert-butoxycarbonylamino)-3-(5-methyl-2-nitrophenoxy)propanoic acid (7.60 g, 83%) as red oil.

1. stirringThe resulting mixture was stirred for 60 min.
2. extractionextracted with EtOAc
3. washThe combined organic extracts were washed with water, brine
4. dry with materialdried over Na2SO4
5. concentrationconcentrated
6. customThe residue was purified by silica gel chromatography