反应详情

To a stirred solution of ethyl 3-mercaptobenzoate (372 mg, 2.03 mmol) in CH2Cl2 (20 mL) under inert atmosphere was added NCS (271 mg, 2.03 mmol) at 0° C.; warmed to RT and stirred for 45 min. To this, compound 2 (500 mg, 1.93 mmol) was added at 0° C.; warmed to RT and stirred for 12 h. The reaction was monitored by TLC; after completion of the reaction, the reaction mixture was diluted with water (40 mL) and extracted with CH2Cl2 (3×20 mL). The combined organic extracts were dried over Na2SO4, filtered and concentrated under reduced pressure to obtain the crude. This was purified by silica gel column chromatography using 10-15% EtOAc/Hexanes to afford compound 3 (700 mg, 83%) as a yellow oil. 1H NMR (400 MHz, CDCl3): δ 7.89 (s, 1H), 7.76-7.74 (m, 1H), 7.72 (s, 1H), 7.68 (s, 1H), 7.49-7.47 (m, 2H), 7.40 (s, 1H), 7.24-7.23 (m, 2H), 7.15 (d, J=8.4 Hz, 1H), 4.32 (q, J=7.2 Hz, 2H), 4.18 (t, J=7.2 Hz, 2H), 2.01-1.96 (m, 2H), 1.34 (t, J=7.2 Hz, 3H), 1.00 (t, J=7.2 Hz, 3H); LC-MS (ESI): 72.2%; m/z 440.4 (M+H+); (column: X Select CSH C-18, 50×3.0 mm, 3.5 μm); RT 4.87 min; 5 mM NH4OAc: ACN; 0.8 mL/min).

1. temperaturewarmed to RT
2. stirringstirred for 12 h
3. customafter completion of the reaction
4. extractionextracted with CH2Cl2 (3×20 mL)
5. dry with materialThe combined organic extracts were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated under reduced pressure
8. customto obtain the crude
9. customThis was purified by silica gel column chromatography