Reaktion #1726703

Reaktionsgleichung

sodium bicarbonate

α-aminophenylacetonitrile hydrochloride

Fmoc-isothiocyanate

ethyldiisopropylamine

→

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

Ausbeute 48.0%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted three times into ethyl acetate
2. 2
   WaschenThe combined organic phases were washed with water and brine
3. 3
   Trocknendried over sodium sulfate
4. 4
   Einengenconcentrated in vacuo

Vorschrift

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%).

Quelle