Реакция #569197

Уравнение реакции

HCl

glycine

triethylamine

indomethacin

HOSu

DCC

→

title product

Выход 70.0%

Indomethacin Glycine

Выход 70.0%

Растворители

water

acetonitrile

water

Условия реакции

Обработка

1. 1
   workup.ADDITIONwere added
2. 2
   workup.STIRRINGstirred for 2 h
3. 3
   Экстракцияextracted with ethyl acetate (80 ml)
4. 4
   СушкаAfter drying (MgSO4) the solution
5. 5
   Другоеwas evaporated to dryness
6. 6
   Другоеto give a yellow solid, which
7. 7
   Другоеwas recrystallised from ethylacetate/hexane

Методика

To a suspension of indomethacin (500 mg, 1.40 mmole) in acetonitrile (20 ml), HOSu (177 mg, 1.54 mmole) and DCC (317 mg, 1.54 mmole) were added and the solution stirred at room temperature for 2 h. A solution of glycine (178 mg, 2.38 mmole) and triethylamine (184 mg, 1.82 mmole) in water (10 ml) was added to the resulting indomethacin hydroxysuccinimide ester and stirred for 2 h, diluted with water (60 ml), acidified with 1M HCl and extracted with ethyl acetate (80 ml). After drying (MgSO4) the solution was evaporated to dryness to give a yellow solid, which was recrystallised from ethylacetate/hexane to give the title product (406 mg, 70% theory) in 95% purity as determined by 1H NMR.

Источник