Ammonium Hydroxide → 5-[4''-(3-Benzyloxy-5-butyl-[1,2,4]triazol-4-ylmethyl)-biphenyl-2-yl]-1H-tetrazole

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Reaction Steps

A solution of 35 mg (0.08 mmole) of 3-n-butyl-5-methylsulfonyl-4-[[2'-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]-4M-1,2,4-triazole (from Example 24) in 300 μl (0.21 mmole) of 0.71 M sodium benzyloxide in benzyl alcohol (freshly prepared from sodium and benzyl alcohol) was stirred at 60° C. for 20 hours, by which time TLC (90:10:1CH2Cl2 --MeOH-concd. NH4OH, developed 3×) indicated complete reaction. The mixture was partitioned between 20 ml of ethyl acetate and 15 ml of 0.2 N HCl. The organic phase was washed with 2×10 ml of 0.2 N HCl, then dried over anhydrous MgSO4, filtered and concentrated in vacuo. The residue was purified by column chromatography on silica gel (elution with 19:1 and then 9:1CH2Cl2 --MeOH). Concentration of clean product fractions yielded 4.4 mg (12%) of the title compound as a residual glass, homogeneous by TLC in 90:10:1 CH2Cl2 --MeOH-concd. NH4OH; mass spectrum (FAB) m/e 466 (M+1)+.

Provenance & Evidence