Réaction #1726703

Équation de réaction

sodium bicarbonate

α-aminophenylacetonitrile hydrochloride

Fmoc-isothiocyanate

ethyldiisopropylamine

→

5-amino-2-(Fmoc-amino)-4-phenylthiazole

Rendement 48.0%

Solvants

DCM

Conditions de réaction

Traitement

1. 1
   Extractionextracted three times into ethyl acetate
2. 2
   LavageThe combined organic phases were washed with water and brine
3. 3
   Séchagedried over sodium sulfate
4. 4
   Concentrationconcentrated in vacuo

Mode opératoire

A suspension of α-aminophenylacetonitrile hydrochloride (3.19 g, 18.9 mmol) and Fmoc-isothiocyanate (5.31 g, 18.9 mmol) in DCM was treated with ethyldiisopropylamine (3.62 ml, 20.8 mmol) at 0° C. for 1 hr and then at ambient temperature for 3 hr. The mixture was poured into saturated aqueous sodium bicarbonate and extracted three times into ethyl acetate. The combined organic phases were washed with water and brine, and dried over sodium sulfate and concentrated in vacuo. Flash chromatography on silica gel (ethyl acetate/hexanes) yielded 5-amino-2-(Fmoc-amino)-4-phenylthiazole (3.75 g, 48%).

Source