Hydrochloric Acid → (S)-2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylic acid

To a solution of (S)-ethyl 2-(3-(4-fluorobenzyl)-4-methyl-2-oxoimidazolidin-1-yl)-4-methylthiazole-5-carboxylate (0.50 g, 1.32 mmol) in tetrahydrofuran (20.0 mL) was added a solution of lithium hydroxide (0.16 g, 6.62 mmol) in water (15 mL). The reaction mixture was refluxed for 16 h and followed by the addition of 1 N aqueous hydrochloric acid solution to adjust pH to 2. The mixture was extracted with ethyl acetate (3×40 mL). The organic layer was washed with saturated aqueous sodium chloride solution (30 mL), dried over anhydrous sodium sulphate and filtered. The filtrate was concentrated in vacuo and the residue was purified by crystallized in ethyl acetate to afford the title compound as a colorless solid (0.32 g, 69%): mp 208-210° C. (ethyl acetate); 1H NMR (300 MHz, CDCl3) δ 7.31-7.26 (m, 2H), 7.04 (dd, J=8.6, 8.6 Hz, 2H), 4.83 (d, J=15.3 Hz, 1H), 4.29-4.14 (m, 2H), 3.78-3.65 (m, 2H), 2.65 (s, 3H), 1.31 (d, J=5.9 Hz, 3H); MS (ES−) m/z 347.9 (M−1).

1. temperatureThe reaction mixture was refluxed for 16 h
2. extractionThe mixture was extracted with ethyl acetate (3×40 mL)
3. washThe organic layer was washed with saturated aqueous sodium chloride solution (30 mL)
4. dry with materialdried over anhydrous sodium sulphate
5. filtrationfiltered
6. concentrationThe filtrate was concentrated in vacuo
7. customthe residue was purified
8. customby crystallized in ethyl acetate

ORD record

ord-e35883fdc4f848939a5e1d4e8b762611

Source dataset

uspto-grants-2011_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08049016B2