Reacción #96279

Ecuación de reacción

(4R)-2-hydroxyphenyl-4-thiazolidinecarboxylic acid

triethylamine

dithiodipropanoic anhydride

→

titled compound

(4R)-3-[3-(2-Carboxyethyldisulfanyl)propanoyl]-2-(2-hydroxyphenyl)-4-thiazolidinecarboxylic acid

Disolventes

acetone

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónextracted with ethyl acetate
2. 2
   workup.ADDITIONafter addition of 50 ml of water containing a small amount of potassium carbonate
3. 3
   Extracciónextracted with ethyl acetate
4. 4
   LavadoThe second organic layer is washed with brine
5. 5
   Secadodried over magnesium sulfate
6. 6
   Otroevaporated in vacuo
7. 7
   OtroThe residual oil is purified by column chromatography on silica gel

Procedimiento

To a stirred solution of 2.0 g of (4R)-2-hydroxyphenyl-4-thiazolidinecarboxylic acid and 1.7 ml of triethylamine in 15 ml of anhydrous acetone, 2.0 g of dithiodipropanoic anhydride is added. The resulting mixture is continuously stirred for 40 min at room temperature and extracted with ethyl acetate after addition of 50 ml of water containing a small amount of potassium carbonate. The aqueous layer is acidified with N aqueous hydrochloric acid and extracted with ethyl acetate. The second organic layer is washed with brine, dried over magnesium sulfate, and evaporated in vacuo. The residual oil is purified by column chromatography on silica gel to give crystals of the titled compound. The yield is 0.6 g (15%).

Fuente