(6E)-7-(3-(4-fluorophenyl)-1-(propan-2-yl)-1H-indol-2-yl)-3,5-dihydroxyhept-6-enoic acid → sodium;(E)-7-[3-(4-fluorophenyl)-1-propan-2-ylindol-2-yl]-3,5-dihydroxyhept-6-enoate

Beteiligte Stoffe

Reaktionsschritte

This example illustrates synthesis of a novel compound of this invention from Fluvastatin. Fluvastatin sodium (5.83 g), which was isolated from Lescol® capsules (commercially available from Novartis Pharmaceuticals, East Hanover, N.J.), was dissolved in 100 mL mixture of methanol and water (50/50, v/v). 50 mL of 10% HCl and 50 mL of methanol were added into the solution and refluxed for 2 hours. Solvent was removed by rotovaping under vacuum to obtain an orange residue. The dry residue (3.23 g) was subjected to silica gel column chromatography twice with hexane/methylene chloride/methanol gradient. The yellow crystals obtained from the fraction 1079-76-3 (Formula II) were re-crystallized with methylene chloride and methanol mixture to produce 1079-76-3C (124 mg). Mass spectrometry and 1H-NMR analysis were performed to identify the fractions as dehydrated methyl ester derivatives of Fluvastatin containing a conjugated all trans triene system in the side chain. 13C-NMR analysis confirmed the provisional structure of 1079-76-3C.

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