反应详情

3-[4-(Azetidin-1-ylcarbonyl)-2-chlorophenoxy]-5-((1S)-2-{[tert-butyl(dimethyl)silyl]oxy}-1-methylethoxy)benzoic acid (3.08 g, 5.93 mmol) was dissolved in methanol (30 mL) and THF (30 mL). Triethylamine (2 mL) was added and the flask evacuated and purged with nitrogen (3 times). 10% Palladium on carbon (200 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for 16 hours LC-MS showed only 26% required product. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, and the flask containing the filtrate evacuated and purged with nitrogen (3 times). Fresh 10% Palladium on carbon (200 mg) was added and the flask further evacuated and finally purged with hydrogen gas. The reaction mixture was stirred at ambient temperature for a further 16 hours LC-MS showed complete reaction. The reaction mixture was evacuated and purged with nitrogen (3 times). The catalyst was filtered off, the filtrate concentrated in vacuo and dissolved in diethylether (50 mL), washed with water (20 mL), 1N citric acid (20 mL), saturated aqueous sodium chloride solution (20 mL) and dried (MgSO4) to give the title compound (2.16 g).

1. customthe flask evacuated
2. custompurged with nitrogen (3 times)
3. addition10% Palladium on carbon (200 mg) was added
4. customthe flask further evacuated
5. customfinally purged with hydrogen gas
6. customThe reaction mixture was evacuated
7. custompurged with nitrogen (3 times)
8. filtrationThe catalyst was filtered off
9. additionthe flask containing the filtrate
10. customevacuated
11. custompurged with nitrogen (3 times)
12. additionFresh 10% Palladium on carbon (200 mg) was added
13. customthe flask further evacuated
14. customfinally purged with hydrogen gas
15. stirringThe reaction mixture was stirred at ambient temperature for a further 16 hours
16. customreaction
17. customThe reaction mixture was evacuated
18. custompurged with nitrogen (3 times)
19. filtrationThe catalyst was filtered off
20. concentrationthe filtrate concentrated in vacuo
21. dissolutiondissolved in diethylether (50 mL)
22. washwashed with water (20 mL), 1N citric acid (20 mL), saturated aqueous sodium chloride solution (20 mL)
23. dry with materialdried (MgSO4)