Propionic Acid → HCID 15093945, compound

Participants

Reaction Steps

HATU (1.41 g, 3.7 mmol) was added to a mixture of ethyl 2-amino-3-oxobutanoate hydrochloride (565 mg, 3.12 mmol) and propionic acid (280 uL, 3.7 mmol) in DMF (2 mL) and THF (4 mL) at RT under N2. The reaction was stirred for 1 h and 4-methylmorpholine (0.41 mL, 3.7 mmol) was then added dropwise via a syringe pump to the above mixture. The reaction was stirred for 1 h and water was then added. It was extracted with EtOAc. The organic layer was washed with saturated sodium bicarbonate, HCl (1 N) and brine, dried over sodium sulfate and concentrated. The residue was purified by ISCO FC with 0-40% EtOAc in hexane to give the title compound (74 mg, 12%) as a light-yellow solid. 1H NMR (400 MHz, CDCl3-d) δ ppm 6.61 (s, 1H) 5.20 (d, J=6.59 Hz, 1H) 4.22 (q, J=7.14 Hz, 2H) 2.34 (s, 3H) 2.26 (q, J=7.51 Hz, 2H) 1.25 (t, J=7.14 Hz, 3H) 1.11 (t, J=7.51 Hz, 3H).

Provenance & Evidence