Propionic Acid → HCID 15093945, compound

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).

1. stirringThe reaction was stirred for 1 h
2. extractionIt was extracted with EtOAc
3. washThe organic layer was washed with saturated sodium bicarbonate, HCl (1 N) and brine
4. dry with materialdried over sodium sulfate
5. concentrationconcentrated
6. customThe residue was purified by ISCO FC with 0-40% EtOAc in hexane

ORD record

ord-365f4011e00241aa85fcc0d3fe32bf04

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08304419B2