Reacción #93718

Ecuación de reacción

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

Disolventes

tetrahydrofuran

Condiciones de reacción

Tratamiento posterior

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

Procedimiento

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.

Fuente