Reacción #445201

Ecuación de reacción

(2R,4R)--2--(2--hydroxyphenyl) --3--(3--mercaptopropionyl)--4--thiazolidinecarboxylic acid

potassium carbonate

ethyl ether

4--(dipropylsulfamoyl)benzoyl chloride

→

titled compound

Rendimiento 58.4%

(2R,4R)--3--[S--[4--(Dipropylsulfamoyl)benzoyl]--3--mercaptopropionyl]--2--(2--hydroxyphenyl)--4--thiazolidinecarboxilic acid

Rendimiento 58.4%

Disolventes

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.ADDITIONAfter the addition the reaction mixture
3. 3
   OtroEther is removed in vacuo and residual solution
4. 4
   ExtracciónProduced oily residue is extracted with ethyl acetate
5. 5
   LavadoThe organic layer is washed with water
6. 6
   Secadodried over anhydrous magnesium sulfate
7. 7
   Concentraciónconcentrated in vacuo
8. 8
   OtroThe resulting residue is purified by silica gel column chromatography

Procedimiento

9.7 g of (2R,4R)--2--(2--hydroxyphenyl) --3--(3--mercaptopropionyl)--4--thiazolidinecarboxylic acid and 12.9 g of potassium carbonate are dissolved in 80 ml of water, and 40 ml of ethyl ether solution of 9.4 g of 4--(dipropylsulfamoyl)benzoyl chloride is added dropwise under ice-cooling. After the addition the reaction mixture is stirred for 1 hour under ice-cooling and for another 1 hour at room temperature. Ether is removed in vacuo and residual solution is adjusted to pH 1 with 6N hydrochloric acid. Produced oily residue is extracted with ethyl acetate. The organic layer is washed with water and dried over anhydrous magnesium sulfate and concentrated in vacuo. The resulting residue is purified by silica gel column chromatography to give 10.5 g of the titled compound as amorphous powder.

Fuente