反应详情

温度

0 °C

4-Methyl-benzoyl isothiocyanate (4.5 ml, 29.5 mmol) was added neat, via syringe under N2 blanket, to a stirred solution of 5-amino-1-tert-butyl-1H-pyrrole-3-carboxylic acid ethyl ester (5.6 g, 26.6 mmol) in anhydrous THF (270 ml), and brought to reflux for 1.5 hours. The solution was chilled to 0° C., then neat N-iodosuccinimide (6.6 g, 29.3 mmol) was added, and the solution was allowed to stir and warm to ambient temperature overnight for 16 hours. Reaction was slowly poured into a stirred 10% (w/v) sodium metabisulfite aqueous solution (200 ml), then extracted with ethyl acetate, dried (MgSO4), and flash chromatographed (silica gel, 25% (v/v) EtOAc/hexanes). Isolated product was crystallized from ethyl acetate/hexanes to afford 4.2 g (41%) of white powder, mp. 200-201° C. MS:M+H=386.

1. temperatureto reflux for 1.5 hours
2. temperaturewarm to ambient temperature overnight for 16 hours
3. customReaction
4. extractionextracted with ethyl acetate
5. dry with materialdried (MgSO4), and flash
6. customchromatographed (silica gel, 25% (v/v) EtOAc/hexanes)
7. customIsolated product was crystallized from ethyl acetate/hexanes