Reaction #1726703

Reaction equation

sodium bicarbonate

α-aminophenylacetonitrile hydrochloride

Fmoc-isothiocyanate

ethyldiisopropylamine

→

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

Yield 48.0%

Solvents

DCM

Conditions

Workup

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

Procedure

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