反应详情

[(R)-[(1S,2S)-1-(4-Acetyl-thiazol-2-ylcarbamoyl)-2-phenyl-propylcarbamoyl]-(4-methoxy-phenyl)-methyl]-carbamic acid tert-butyl ester (3.1 g, 5.2 mmol) was stirred in dichloromethane (50 mL) in an ice-bath. Trifluoroacetic acid (50 mL) was added and the solution was stirred for 1 hour. The reaction mixture was evaporated and the residue was precipitated with hexanes/ether. The mixture was stirred vigorously for 10 minutes and then filtered. The solid was partitioned between aqueous sodium bicarbonate and dichloromethane. The organic layer was separated and the aqueous layer extracted with dichloromethane. The combined organic extracts were washed with brine and dried (sodium sulfate). Evaporation of the solvents gave (2S,3S)-N-(4-acetyl-thiazol-2-yl)-2-[(R)-2-amino-2-(4-methoxy-phenyl)-acetylamino]-3-phenyl-butyramide (2.7 g, 90% pure) as a white solid.

1. customThe reaction mixture was evaporated
2. customthe residue was precipitated with hexanes/ether
3. stirringThe mixture was stirred vigorously for 10 minutes
4. filtrationfiltered
5. customThe solid was partitioned between aqueous sodium bicarbonate and dichloromethane
6. customThe organic layer was separated
7. extractionthe aqueous layer extracted with dichloromethane
8. washThe combined organic extracts were washed with brine
9. dry with materialdried (sodium sulfate)
10. customEvaporation of the solvents