反应详情

To a 100-mL round-bottomed flask was added ethyl 3-methoxyphenylalaninate (526 mg, 2.35 mmol), 2-(tert-butoxycarbonylamino)acetic acid (454 mg, 2.59 mmol, Sigma-Aldrich, St. Louis, Mo.), HATU (1.07 g, 2.82 mmol, Sigma-Aldrich, St. Louis, Mo.), Hünig's base (0.819 mL, 4.71 mmol) and DMF (5 mL). The reaction mixture was stirred at room temperature for 2 h then diluted with water (30 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated aqueous NaCl (30 mL) and dried over Na2SO4. The solution was filtered and concentrated in vacuo to give the crude material as light-yellow oil. The crude product was purified by silica gel chromatography, eluting with 60% EtOAc in hexanes to give ethyl N-(tert-butoxycarbonyl)glycyl-3-methoxyphenylalaninate (822 mg).

1. extractionextracted with EtOAc (2×50 mL)
2. extractionThe organic extract
3. washwas washed with saturated aqueous NaCl (30 mL)
4. dry with materialdried over Na2SO4
5. filtrationThe solution was filtered
6. concentrationconcentrated in vacuo
7. customto give the crude material as light-yellow oil
8. customThe crude product was purified by silica gel chromatography
9. washeluting with 60% EtOAc in hexanes