Reaction #6430

Reaction equation

methyl succinimidyl adipate

chlorotrimethylsilane

sodium iodide

→

adipic acid monosuccinimidyl ester

Yield 75.2%

Solvents

acetonitrile

ethyl acetate

Conditions

Workup

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

Procedure

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