反应详情

To methylthiosalicylate (3.92 mL, 28.5 mmol) in DMF at 0° C. was added triethylamine (3.97 mL, 28.5 mmol) then cyclobutyl bromide (5.00 g, 37.0 mmol). The ice bath was removed and the reaction was stirred at rt for 1 h then heated to 50° C. overnight. After cooling to rt, diethyl ether was added and the mixture was filtered. The filtrate was diluted with ethyl acetate, then washed with water (6×) and brine (1×). The organic layer was dried (MgSO4), filtered and concentrated to provide a yellow oil. The yellow oil was dissolved in CH2Cl2 (143 mL) and MCPBA (˜75%, 19.7 g, ca. 85.5 mmol) was added. The reaction was stirred for 2.5 h, then was cooled to 0° C. 1 N NaOH was added, and the reaction was stirred for 5 min. The layers were separated, and the organic layer was washed with 1 N NaOH (2×). The aqueous layer was back-extracted with CH2Cl2. The combined organic layers were washed with brine, dried (MgSO4), filtered and concentrated to provide 2A as a clear oil (7.20 g). LC-MS: 255.01 (M+H)+.

1. customThe ice bath was removed
2. temperaturethen heated to 50° C. overnight
3. temperatureAfter cooling to rt
4. additiondiethyl ether was added
5. filtrationthe mixture was filtered
6. additionThe filtrate was diluted with ethyl acetate
7. washwashed with water (6×) and brine (1×)
8. dry with materialThe organic layer was dried (MgSO4)
9. filtrationfiltered
10. concentrationconcentrated
11. customto provide a yellow oil
12. stirringThe reaction was stirred for 2.5 h
13. temperaturewas cooled to 0° C
14. stirringthe reaction was stirred for 5 min
15. customThe layers were separated
16. washthe organic layer was washed with 1 N NaOH (2×)
17. extractionThe aqueous layer was back-extracted with CH2Cl2
18. washThe combined organic layers were washed with brine
19. dry with materialdried (MgSO4)
20. filtrationfiltered
21. concentrationconcentrated