Réaction #93713

Équation de réaction

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

dicyclohexyl carbodiimide

DBU

(R)-glycidic acid

N-allyl-N-phenylthiomethylammonium chloride

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

→

title compound

N-allyl-N-phenylthiomethyl-(R)-glycidic acid amide

Solvants

tetrahydrofuran

methylene chloride

Conditions de réaction

Traitement

1. 1
   Autreat 0°
2. 2
   FiltrationThe crystalline dicyclohexylurea is filtered off with suction, methylene chloride
3. 3
   workup.ADDITIONis added to the filtrate
4. 4
   Lavagethe whole is washed with phosphate buffer
5. 5
   AutreThe crude product obtained from the organic phase
6. 6
   Séchageby drying over sodium sulphate and concentration by evaporation in vacuo
7. 7
   Autreis chromatographed over 500 g of silica gel

Mode opératoire

Analogously to Example 5, 8.45 g (50 mmol) of 2-(S)-bromo-3-hydroxypropionic acid in 200 ml of tetrahydrofuran is converted using 15.2 g (100 mmol) of 1,5-diazabicyclo[5.4.0]undec-5-ene into the DBU salt of (R)-glycidic acid. To the latter there are added in situ in methylene chloride at room temperature, 10.31 g (50 mmol) of dicyclohexyl carbodiimide and then, at 0°, 10.75 g (50 mmol) of N-allyl-N-phenylthiomethylammonium chloride. The resulting mixture is stirred for a further 3 hours at room temperature. The crystalline dicyclohexylurea is filtered off with suction, methylene chloride is added to the filtrate and the whole is washed with phosphate buffer having a pH of 8.0. The crude product obtained from the organic phase by drying over sodium sulphate and concentration by evaporation in vacuo is chromatographed over 500 g of silica gel using toluene/ethyl acetate (9:1) and the pure title compound is obtained in the form of a colourless oil.

Source