Reacción #6430

Ecuación de reacción

methyl succinimidyl adipate

chlorotrimethylsilane

sodium iodide

→

adipic acid monosuccinimidyl ester

Rendimiento 75.2%

Disolventes

acetonitrile

ethyl acetate

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaat reflux for 12 hours
2. 2
   LavadoThe reaction mixture was washed repeatedly with 5 percent aqueous sodium bisulfite until the organic solution
3. 3
   LavadoThen it was washed with brine
4. 4
   Secadodried over anhydrous magnesium sulfate
5. 5
   Filtraciónfiltered
6. 6
   Concentraciónconcentrated

Procedimiento

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.

Fuente