反応 #49183

反応方程式

compound 41a

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

diisopropyl carbodiimide

pentafluoro phenol

→

Compound 43a

収率 101.3%

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

収率 101.3%

溶媒

dichloromethane

反応条件

後処理

1. 1
   その他After overnight the reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONTo the residue ethyl acetate (100 mL) was added
3. 3
   ろ過the filtered
4. 4
   その他to remove diisopropyl urea
5. 5
   洗浄The precipitate was washed with ethyl acetate (50 mL)
6. 6
   洗浄The combined organic layer was washed with saturated sodium bicarbonate and water
7. 7
   乾燥The organic layer was dried over sodium sulfate
8. 8
   ろ過filtered
9. 9
   その他evaporated to dryness

実験手順

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.

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