反应详情

To a stirred solution of compound 1b, e.g., N-(2-amino-2-oxo-1-phenylethyl)-3-(biphenyl-4-ylsulfonyl)-1,3-thiazolidine-2-carboxamide (385 mg, 0.8 mmol) in DMF (1 mL) at RT was added cyanuric chloride (74 mg, 0.4 mmol) in one portion. After one night, the reaction was done. Water (3 mL) was added and a precipitate was formed. The aqueous phase was extracted with two portions of EtOAc (5 mL). Combined organic phases were washed with 5% aqueous sodium bicarbonate, with water, dried over MgSO4 and concentrated under reduced pressure. A light yellow solid was isolated and was purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1), affording product Ic, e.g., 3-(biphenyl-4-ylsulfonyl)-N-[cyano(phenyl)methyl]-1,3-thiazolidine-2-carboxamide (257 mg, 69% yield) in 100% purity by HPLC.

1. waitAfter one night
2. customa precipitate was formed
3. extractionThe aqueous phase was extracted with two portions of EtOAc (5 mL)
4. washCombined organic phases were washed with 5% aqueous sodium bicarbonate, with water
5. dry with materialdried over MgSO4
6. concentrationconcentrated under reduced pressure
7. customA light yellow solid was isolated
8. customwas purified by flash chromatography (Cyclohexane/EtOAc gradient form 8:2 to 1:1)