A-Benzyl Tetracyclic-based Medicaments

Secretory Phospholipase A2 Inhibitors A. (V-Benzyl Tetracyclic-based Medicaments Title sPLA2 Inhibitors 

Beight et al., US Patent 6,992,100 (January 31, 2006) Assignee Eli Lilly and Company Utility Treatment or Prevention of Sepsis 

Invention Significance Human nonpancreatic secretory phospholipase-A2 

A solution of 1-methoxynaphthalene (126.6 mmol) dissolved in 100 ml THF was treated with n-butyllithium (132.9 mmol) over 5 minutes at ambient temperature, then cooled to -50°C, and triisopropyl borate (190 mmol) added dropwise over 15 minutes. The resulting solid was treated with 100 ml THF, then warmed to 0°C, and poured into 100 ml 1M HC1. The mixture was extracted with EtOAc, then dried using Na2S04, concentrated, and the residue partially dissolved in diethyl ether. It was then triturated with hexane, washed with hexane, and the product isolated in 41% yield as an off-white crystalline solid. 

Preparation of 2-(l-methoxynaphthalen-2-yl)-3-nitrobenzoic acid, methyl ester 

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