반응 #93718

반응 방정식

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

p-methoxybenzyl-tert.-butylthiomethylammonium chloride

N-p-methoxybenzyl-N-tert-butylthiomethylammonium chloride

dicyclohexyl carbodiimide

triethylamine

→

title compound

N-p-methoxybenzyl-N-tert.-butylthiomethyl-2-(S)-bromo-3-hydroxypropionic acid amide

용매

tetrahydrofuran

반응 조건

후처리

1. 1
   기타the dicyclohexylurea that has precipitated
2. 2
   여과is filtered off with suction
3. 3
   농축The filtrate is concentrated by evaporation under reduced pressure
4. 4
   기타the residue is chromatographed over 500 g of silica gel

실험 절차

4.13 g (20 mmol) of dicyclohexyl carbodiimide and 2.79 ml (20 mmol) of triethylamine are added at room temperature while stirring to a mixture of 3.38 g (20 mmol) of 2-(S)-bromo-3-hydroxypropionic acid and 5.151 g (20 mmol) of p-methoxybenzyl-tert.-butylthiomethylammonium chloride (Example 24) in 100 ml of tetrahydrofuran. The mixture is stirred for two hours at room temperature and the dicyclohexylurea that has precipitated is filtered off with suction. The filtrate is concentrated by evaporation under reduced pressure and the residue is chromatographed over 500 g of silica gel using toluene/ethyl acetate (9:1). The title compound is obtained in the form of a colourless, viscous oil.

출처