Triethylamine → HCID 69053466, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 3-(4-benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-propionic acid (500 mg, 1.25 mmol), HOBt (180 mg, 2.5 mmol), and EDCI (480 mg, 2.5 mmol) in DMF (3 mL) was stirred at 0° C. for 0.5 h. To this mixture was added 1-amino-2-propanone hydrochloride (4) (272 mg, 2.5 mmol) followed by Et3N (550 □L, 0.6 mmol). The mixture was stirred at 0° C. for 0.5 h and at room temperature for 1 h. Water (10 mL) was added, and the product was extracted with EtOAc (3×15 mL). The combined extracts were dried over Na2SO4 and concentrated, and the residue was triturated with water to obtain 3-(4-benzyloxy-phenyl)-2-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-N-(2-oxo-propyl)-propionamide (5) as a solid (500 mg, 88%). 1H NMR (CDCl3): □7.78 (m, 2H), 7.70 (m, 2H), 7.35 (m, 4H), 7.1 (d, 2H), 6.8 (m, 3H), 4.92 (s, 2H), 4.2 (m, 2H), 3.6 (d, 2H), 2.2 (s, 3H); ). LCMS m/z 457.1 (M+1)

Provenance & Evidence