Diisopropylethylamine → HCID 86664833, compound

Participants

Reaction Steps

To a solution of methyl 3-amino-5-(pyridin-4-yl)benzoate 45.1.C (4.70 g, 20.6 mmol) in DMF (50 mL) was added (S)-2-(tert-butoxycarbonyl)-3-phenylpropanoic acid (6.56 g, 24.7 mmol, available from Aldrich), diisopropylethylamine (5.40 mL, 30.9 mmol) and 2-(1H-Benzotriazole-1-yl)-1,1,3,3-Tetramethyluronium hexafluorophosphate (9.36 g, 24.7 mmol). The resulting mixture is stirred overnight at room temperature. The mixture was then partitioned between water and EtOAc. The layers were separated, and the aqueous phase was extracted with additional EtOAc. The combined organic layers were washed with water and brine, dried (MgSO4), and concentrated. The residue was purified by silica gel flash chromatography (0-100% EtOAc/hexane) to afford (S)-methyl 3-(2-(tert-butoxycarbonyl)-3-phenylpropanamido)-5-(pyridin-4-yl)benzoate 45.1.D (3.00 g, 31% yield).

Provenance & Evidence