Reaktion #462466

Reaktionsgleichung

(-)-1-(N-t-butylacetamido)-3-amino-5,7-diphenylhexahydroazepin-2-one

m-tolylisocyanate

→

(-)-1-(N-t-butylacetamido)-3-(3-tolylureido)-5,7-diphenylhexahydroazepin-2-one

Lösungsmittel

ethyl acetate

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeTo a 35 mL round-bottomed flask equipped with N2 inlet and condenser
2. 2
   TemperaturThe reaction was refluxed for 2.5 hr
3. 3
   Temperaturcooled
4. 4
   Sonstigeevaporated
5. 5
   SonstigeThe residue was chromatographed on silica gel
6. 6
   Sonstigeto afford an oil which
7. 7
   Sonstigewas crystallized from methylene chloride/isopropyl ether to a give mp 140°-150° C., 71 mg (18%), αD =-18.6° (c=1, CH2Cl2)

Vorschrift

To a 35 mL round-bottomed flask equipped with N2 inlet and condenser were added 293 mg (0.745 mmol) (-)-1-(N-t-butylacetamido)-3-amino-5,7-diphenylhexahydroazepin-2-one, 10 mL ethyl acetate, and 0.096 mL (0.745 mmol) m-tolylisocyanate. The reaction was refluxed for 2.5 hr, cooled, and evaporated. The residue was chromatographed on silica gel using hexane/ethyl acetate as eluant to afford an oil which was crystallized from methylene chloride/isopropyl ether to a give mp 140°-150° C., 71 mg (18%), αD =-18.6° (c=1, CH2Cl2). The Rf value on TLC and 1H-NMR spectrum match those of the racemate.

Quelle