[C:1]1([C:7]2[NH:8][C:9]([SH:12])=[N:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].Br[CH:16]([CH2:21][CH:22]([CH3:24])[CH3:23])[C:17]([O:19][CH3:20])=[O:18]>CN(C=O)C.C(OCC)C.O.C(=O)(O)[O-]>[CH3:23][CH:22]([CH3:24])[CH2:21][CH:16]([S:12][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:11][N:10]=1)[C:17]([O:19][CH3:20])=[O:18]5-Phenyl-4H-1,2,4-triazole-3-thiol (296 mg, 1.67 mmoles) in 5 mL of DMF was treated with sodium hydride (67 mg, 60% oil dispersion, 1.76 mmoles) and stirred for 30 minutes. Methyl 2-bromo-4-methylpentanoate (275 μL, 1.67 mmoles) was added in one portion and the reaction was stirred overnight. The reaction was diluted with diethyl ether, water and sat. aq. bicarbonate. The phases were separated and the organic phase was washed with 2 portions of 1.2 N hydrochloric acid and then brine. The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to afford a residue which was purified by flash chromatography to give methyl 4-methyl-2-[(5-phenyl-4H-1,2,4-triazol-3-yl)sulfanyl]pentanoate.
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