Réaction #6430

Équation de réaction

methyl succinimidyl adipate

chlorotrimethylsilane

sodium iodide

→

adipic acid monosuccinimidyl ester

Rendement 75.2%

Solvants

acetonitrile

ethyl acetate

Conditions de réaction

Traitement

1. 1
   Températureat reflux for 12 hours
2. 2
   LavageThe reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution
3. 3
   LavageThen it was washed with brine
4. 4
   Séchagedried over anhydrous magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated

Mode opératoire

A solution of methyl succinimidyl adipate (4.5 g, 17.5 mmol), chlorotrimethylsilane (11.1 ml, 87.5 mmol) and sodium iodide (13.1 g, 87.5 mmol) in 10 ml of acetonitrile was heated at reflux for 12 hours. The mixture was then cooled to room temperature and diluted with ethyl acetate. The reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution was colorless. Then it was washed with brine, dried over anhydrous magnesium sulfate, filtered and concentrated to provide 3.2 g (71 percent yield by weight) of adipic acid monosuccinimidyl ester as a white solid.

Source