Isosorbide-2-Acetate

Chemical Properties

Isosorbide-2-acetate is a colourless, crystalline substance with a melting point of 75°-76°C. It has a TLC (diethyl ether) value of Rf=0.28 and a specific rotation of [α]D 20 =+77.1° (c=1.12, ethyl acetate). It is an important intermediate in the synthesis of isosorbide-5-mononitrate, a well-known organic nitrate drug.

Uses

1,4:3,6-Dianhydro-2-O-acetyl-D-glucitol is a useful reagent in the practical enzymic synthesis of isosorbide-2-acetate.

Preparation

The synthesis of isosorbide-2-acetate involves dissolving 2.30 g (10 mmol) of isosorbide-2,5-diacetate in 15 ml of acetone and 5 ml of n-heptanol. Then, 200 mg of lipase from Pseudomonas fluorescens (SAM II, Amano Pharmaceuticals) is added, and the mixture is stirred at room temperature for 2 days. After that, the enzyme is removed by filtration, and the resulting solid is washed thoroughly with acetone. The solvent, excess n-heptanol, and heptyl acetate residue are removed by distillation.
The yield is 1.71 g (9.09 mmol) of isosorbide-2-acetate, which is a colourless crystalline substance with a melting point of 75°-76°C. The overall yield is 91%.
US5538891A