تفاعل #49183

معادلة التفاعل

compound 41a

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

diisopropyl carbodiimide

pentafluoro phenol

→

Compound 43a

المردود 101.3%

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

المردود 101.3%

المذيبات

dichloromethane

ظروف التفاعل

المعالجة

1. 1
   أخرىAfter overnight the reaction mixture was evaporated to dryness
2. 2
   workup.ADDITIONTo the residue ethyl acetate (100 mL) was added
3. 3
   ترشيحthe filtered
4. 4
   أخرىto remove diisopropyl urea
5. 5
   غسيلThe precipitate was washed with ethyl acetate (50 mL)
6. 6
   غسيلThe combined organic layer was washed with saturated sodium bicarbonate and water
7. 7
   تجفيفThe organic layer was dried over sodium sulfate
8. 8
   ترشيحfiltered
9. 9
   أخرىevaporated to dryness

الإجراء التجريبي

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.

المصدر