Hydrochloric Acid → 2-Ethoxy-1-((2'-(1-(triphenylmethyl)-1H-tetrazol-5-yl)(1,1'-biphenyl)-4-yl)methyl)-1H-benzimidazole-7-carboxylic acid

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In methylene chloride (183 kg) was suspended 2-ethoxy-1-[[2′-(1H-tetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid [Compound A] (480 kg) obtained in Reference Example 8. To the suspension was added triethylamine (13.8 kg) to dissolve Compound A. To the solution was added triphenylmethylchloride (34.9 kg) in methylene chloride solution (50 L) and the solution was heated for about 6 hours under reflux (40° C.). To the solution was added methylene chloride (273 kg) and the solution was allowed to stand at room temperature for one night. The reaction solution was heated at 30-35° C., to which was added methanol (81.4 kg). To the solution was added water (205 kg) and the solution was adjusted to pH 3.1±0.2 with 1N hydrochloric acid. The organic layer was separated and concentrated to 288 kg. The concentrate was stirred at room temperature for about 30 minutes, to which was dropped hexane (68 kg) for 20±5 minutes. The resulting mixture was stirred at room temperature for about 30 minutes, followed by at 5±5° C. for about 1 hour. The crystals were separated and washed with a mixture of hexane-methylene chloride (5:1) (205 L). The wet crystals were dissolved in DMF(183 L) and the solution was evaporated to about 138 kg or less to give 2-ethoxy-1-[[2′-(N-triphenylmethyltetrazol-5-yl)biphenyl-4-yl]methyl]benzimidazole-7-carboxylic acid [Compound A(T)] solution (89%).

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