반응 #741190

반응 방정식

dicyclohexylcarbodiimide

2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine

hydroxybenzotriazole

2-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acid

→

2-[N-(2,4,6-Trifluorophenyl)sulfamoyl]-acetic acid-[2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamide]

용매

DMF

반응 조건

후처리

1. 1
   기타The turbid reaction solution
2. 2
   여과is then filtered
3. 3
   기타the clear filtrate is evaporated to dryness in a vacuum
4. 4
   workup.DISSOLUTIONThe residue is dissolved in 100 ml of ethyl acetate
5. 5
   workup.STIRRINGthe solution is shaken out five times with saturated sodium bicarbonate solution
6. 6
   건조The ethyl acetate solution is dried on sodium sulfate
7. 7
   여과filtered
8. 8
   기타evaporated to dryness
9. 9
   기타The residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/methylene chloride 8:2
10. 10
    기타The corresponding fractions together contain 0.62 g (1.42 mmol)=45% of the theoretical yield of product is obtained as an amorphous solid

실험 절차

1.38 g (3.16 mmol) of 2-[N-(2,4,6-trifluorophenyl)sulfamoyl] acetic acid is dissolved in 20 ml of DMF with exclusion of moisture and under argon atmosphere, 509 mg (3.16 mmol) of 2-hydroxy-2-(2,2-dimethyl-1,3-dioxolan-4-yl)-ethylamine and 484 mg (3.16 mmol) of hydroxybenzotriazole are added and the solution is cooled to -10° C. 652 mg (3.16 mmol) of dicyclohexylcarbodiimide is added to the cooled solution, it is stirred for one hour at -10° C and for 12 more hours at room temperature. The turbid reaction solution is then filtered and the clear filtrate is evaporated to dryness in a vacuum. The residue is dissolved in 100 ml of ethyl acetate and the solution is shaken out five times with saturated sodium bicarbonate solution and twice with water. The ethyl acetate solution is dried on sodium sulfate, filtered and evaporated to dryness. The residue is chromatographed on silica gel 60 (Merck) with ethyl acetate/methylene chloride 8:2. The corresponding fractions together contain 0.62 g (1.42 mmol)=45% of the theoretical yield of product is obtained as an amorphous solid.

출처