反应详情

温度

20 °C

4-Acetyl-3-{[(S)-cyclopropyl-(3-fluoro-phenyl)-methyl]-amino}-8-fluoro-2-benzopyran-1-one (14.30 g, 38.72 mmol) was dissolved in a mixture of tetrahydrofuran (50 mL) and methanol (50 mL) and placed on an ice/water bath with stirring. NaOH (1 M in H2O, 100 ml) was added and stirring continued for 1 hour. The cold bath removed and the mixture was allowed to warm to r.t. (20° C.) during 1 hour. The reaction mixture was poured into ice-water mixture (200 g+200 ml), followed by slow addition of 2 M aq. HCl (200 mL) and extracted with ethyl acetate (200 mL), washed with sat. aq. NaCl, dried (Na2SO4), filtered and evaporated to give the title compound (14.65 g, yield 97.7%) as a pale brown foam. The crude product was used in the next step without further purification. LC-MS (m/z) 388.3 (MH+); tR=1.2. 1H NMR (500 MHz, DMSO-d6): a mixture of tautomers and diastereoisomers. The following compounds were prepared analogously:

1. customplaced on an ice/water bath
2. stirringstirring
3. customThe cold bath removed
4. additionThe reaction mixture was poured into ice-water mixture (200 g+200 ml)
5. additionfollowed by slow addition of 2 M aq. HCl (200 mL)
6. extractionextracted with ethyl acetate (200 mL)
7. washwashed with sat. aq. NaCl
8. dry with materialdried (Na2SO4)
9. filtrationfiltered
10. customevaporated