OCCC[N:5]1C(=O)N(CCOC2C=CC=CC=2)C(CC)=[N:6]1.[S:22]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)([O-:25])(=[O:24])=[O:23].C([N:35](CC)[CH2:36][CH3:37])C.S(Cl)(C1C=CC(C)=CC=1)(=O)=[O:41]>C(Cl)Cl.CN(C1C=CN=CC=1)C.O>[S:22]([C:26]1[CH:32]=[CH:31][C:29]([CH3:30])=[CH:28][CH:27]=1)([OH:25])(=[O:24])=[O:23].[N:35]1[N:5]=[N:6][C:37](=[O:41])[CH:36]=1
The alcohol is converted to the tosylate by dissolving in methylene chloride containing N,N-dimethyl-4-aminopyridine (0.05 mol eq) and triethylamine (1.05 mol eq) and treating with tosyl chloride (1.1 mole eq) added in one portion at 0° C. with stirring. After standing for about 24 hr. at 0° C., the mixture is treated with water and extracted several times with methylene chloride. The combined methylene chloride extracts are dried over magnesium sulfate, filtered and concentrated under reduced pressure. Flash chromatography of residual material affords 2-[3-(p-toluenesulfonate)propyl]-5-ethyl-2,4-dihydro-4-(2-phenoxyethyl)-3H-1,2,4-triazol-3-one (XV, Y=H, X1 =0, n=2, R2 =C2H5).
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