반응 #49183

반응 방정식

compound 41a

6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic acid

diisopropyl carbodiimide

pentafluoro phenol

→

Compound 43a

수율 101.3%

6-(1,3-Dioxo-1,3-dihydro-isoindol-2-yl)-hexanoic acid pentafluorophenyl ester

수율 101.3%

용매

dichloromethane

반응 조건

후처리

1. 1
   기타After overnight the reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONTo the residue ethyl acetate (100 mL) was added
3. 3
   여과the filtered
4. 4
   기타to remove diisopropyl urea
5. 5
   세척The precipitate was washed with ethyl acetate (50 mL)
6. 6
   세척The combined organic layer was washed with saturated sodium bicarbonate and water
7. 7
   건조The organic layer was dried over sodium sulfate
8. 8
   여과filtered
9. 9
   기타evaporated to dryness

실험 절차

Referring to scheme 12, compound 41a (13.3 g, 51 mmol) was dissolved in anhydrous dichloromethane (40 mL) and cooled to 0° C. under argon. To the solution were added diisopropyl carbodiimide (6.31 g, 7.7 mL, 50 mmol) and pentafluoro phenol (42, 9.2 g, 50 mmol). After overnight the reaction mixture was evaporated to dryness. To the residue ethyl acetate (100 mL) was added and the filtered to remove diisopropyl urea. The precipitate was washed with ethyl acetate (50 mL). The combined organic layer was washed with saturated sodium bicarbonate and water. The organic layer was dried over sodium sulfate, filtered and evaporated to dryness. Compound 43a (Rf=0.8 in 10% EtOAc/Hexane, 21.65 g, 92%) was obtained, which was directly used for the next step without further purification.

출처