[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7]C(=NC#N)OC2C=CC=CC=2)[CH:2]=1.[C:19]1([C@H:25]([CH2:27][OH:28])[NH2:26])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C[N:30]1CCOCC1.C(O)(C)C>CO.C(Cl)(Cl)Cl>[C:19]1([C@@H:25]2[CH2:27][O:28][N:30]([NH:7][C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[NH:26]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1A stirred mixture of N-(3-pyridyl)-N'-cyano-O-phenylisourea (see, Example 5 for procedure) (3.00 g, 0.0126 mol), (R)-2-phenylglycinol (1.9 g, 0.0130 mol), N-methylmorpholine (30 mL), and isopropanol (20 mL) was refluxed, under nitrogen, for 2 hours; the reaction was complete by TLC with 10% MeOH-CHCl3. The mixture was concentrated and the residue was chromatographed on silica gel with 1-6% MeOH-CHCl3. The first product eluted from the column was crystallized from MeOH-EtOAc to give 261 mg of (R)-4,5-dihydro-4-phenyl-2-(3-pyridyl)aminooxadiazole: mp 125°-130° C.
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