Tetrahydrofuran → (S)-2-(2-Oxo-2H-pyridin-1-yl)-propionic acid

A stirred mixture of (S)-2-(2-Oxo-2H-pyrid-1-yl)-propionic acid ethyl ester (364 mg, 1.87 mmol), THF (2 ml), water (1 ml) and sodium hydroxide (90 mg, 2.24 mmol) was kept at room temperature for 1 h, then concentrated under reduced pressure. The residue was dissolved in ether and the resulting solution washed with water. The organic layer was discarded and the aqueous layer was acidified with concentrated HCl then extracted several times with ethyl acetate. The combined organic extracts were dried (MgSO4), filtered and concentrated. The residue was triturated with ether to afford the title compound as a colorless solid (84 mg, 27%): [α]31D=−50° (c=0.2, CH3OH); 1H NMR (400 MHz, DMSO) δ 1.5 (3H, d), 5.1 (1H, q), 6.2 (1H, t), 6.4 (1H, d), 7.4 (1H, m), 7.6 (1H, d).

1. concentrationconcentrated under reduced pressure
2. dissolutionThe residue was dissolved in ether
3. washthe resulting solution washed with water
4. extractionthen extracted several times with ethyl acetate
5. dry with materialThe combined organic extracts were dried (MgSO4)
6. filtrationfiltered
7. concentrationconcentrated
8. customThe residue was triturated with ether

ORD record

ord-85745ad5bdfc47c0aa199427ac65b275

Source dataset

uspto-grants-2012_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08093392B2