N-(tert-butoxycarbonyl)glycine → ethyl N-(tert-butoxycarbonyl)glycyl-3-(6-methoxy-2-pyridinyl)alaninate

Participants

Reaction Steps

To a 100-mL round-bottomed flask was added ethyl 3-(6-methoxy-2-pyridinyl)alaninate (1.045 g, 4.66 mmol), N-boc-glycine (0.898 g, 5.13 mmol, Aldrich, St. Louis, Mo.), HATU (2.126 g, 5.59 mmol, Aldrich, St. Louis, Mo.), and N,N-diisopropylethylamine (2.43 mL, 13.98 mmol, Aldrich, St. Louis, Mo.) in DMF (5 mL). The reaction mixture was stirred at room temperature for 3 h. The reaction mixture was diluted with water (40 mL) and extracted with EtOAc (2×50 mL). The organic extract was washed with saturated 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 70% EtOAc/hexanes to give ethyl N-(tert-butoxycarbonyl)glycyl-3-(6-methoxy-2-pyridinyl)alaninate (1.29 g) as a colorless oil.

Provenance & Evidence