反应详情

To tert-butyl 4-(2-(3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)ureido)ethyl)piperidine-1-carboxylate (0.29 g, 0.4 mmol) dissolved in DCM (2 ml) was added TFA (0.5 ml, 7 mmol). The resulting mixture was stirred at room temperature for 2 hours. After this time the mixture was concentrated under reduced pressure and the residue triturated with diethyl ether. The pale yellow solid was filtered, washed with ether and dried under vacuum. This solid TFA salt was partitioned between DCM and saturated aqueous NaHCO3. The aqueous was re-extracted with DCM (×2). The combined organic extracts were dried over MgSO4 and concentrated up. The residue was taken up in dry DCM and HCl (2M in diethyl ether) was added. The cloudy solution was conc under reduced pressure and dried under high vac to give 3-(5-chloro-4-(4-(methylsulfonamido)phenyl)thiazol-2-yl)-1-(3,3-diphenylpropyl)-1-(2-(piperidin-4-yl)ethyl)urea HCl salt 51 as a pale yellow solid.

1. concentrationAfter this time the mixture was concentrated under reduced pressure
2. customthe residue triturated with diethyl ether
3. filtrationThe pale yellow solid was filtered
4. washwashed with ether
5. customdried under vacuum
6. customThis solid TFA salt was partitioned between DCM and saturated aqueous NaHCO3
7. extractionThe aqueous was re-extracted with DCM (×2)
8. dry with materialThe combined organic extracts were dried over MgSO4
9. concentrationconcentrated up
10. additionHCl (2M in diethyl ether) was added
11. customdried under high vac