Reacción #93710

Ecuación de reacción

dicyclohexyl carbodiimide

1,5-diazabicyclo[5.4.0]-undec-5-ene

2-(S)-bromo-3-hydroxypropionic acid

N-benzyl-N-tert.-butylthiomethylammonium chloride

→

dicyclohexylurea

Disolventes

tetrahydrofuran

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.DISTILLATIONThe solvent is subsequently distilled off in vacuo and 25 ml of methylene chloride
2. 2
   workup.ADDITIONare added
3. 3
   workup.ADDITIONTo this solution containing the DBU salt of (R)-glycidic acid
4. 4
   workup.STIRRINGafter stirring for one hour
5. 5
   workup.ADDITIONAfter the addition of the last-mentioned reaction component

Procedimiento

5 ml of a 2M solution of 1,5-diazabicyclo[5.4.0]-undec-5-ene (DBU) in tetrahydrofuran are added while stirring, at room temperature, to a solution of 845 mg (5 mmol) of 2-(S)-bromo-3-hydroxypropionic acid in 10 ml of absolute tetrahydrofuran and the resulting mixture is stirred for a further 2 hours at room temperature. The solvent is subsequently distilled off in vacuo and 25 ml of methylene chloride are added. To this solution containing the DBU salt of (R)-glycidic acid there are added 1.03 g (5 mmol) of dicyclohexyl carbodiimide and, after stirring for one hour, 1.3 g (5 mmol) of N-benzyl-N-tert.-butylthiomethylammonium chloride. After the addition of the last-mentioned reaction component, crystalline dicyclohexylurea is formed. After a reaction time of 3 hours at room temperature, the latter is filtered off with suction and the filtrate is diluted with methylene chloride and washed with phosphate buffer solution having a pH of 8. After concentration of the organic phase by evaporation, the residue is chromatographed over 50 g of silica gel. After a few first fractions have been removed with toluene, the title compound is eluted with a mixture of toluene/ethyl acetate (9:1) in the form of a colourless, viscous oil.

Fuente