m-Tolyl isocyanate → HCID 19037591, compound

Participants

Reaction Steps

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.

Provenance & Evidence