(3R,5S,E)-7-(2-cyclopropyl-4-(4-fluorophenyl)quinolin-3-yl)-3,5-dihydroxy-N-((S)-1-phenylethyl)hept-6-enamide → (E)-(3R,5S)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide

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can be prepared from (E)-(R)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3-hydroxy-5-oxo-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide according to the procedures described above for the preparation of (E)-(3R,5S)-7-[2-Cyclopropyl-4-(4-fluoro-phenyl)quinolin-3-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide. Chromatography on silicagel with ethyl acetate/hexanes (9:1) as eluent affords (E)-(3R,5S)-7-[3-(4-Fluoro-phenyl)-1-isopropyl-1H-indol-2-yl]-3,5-dihydroxy-hept-6-enoic acid ((S)-1-phenyl-ethyl)-amide as a light yellow foam. Rf=0.175 (TLC on silicagel, ethyl acetate/hexanes 9:1 as eluent). [α]D20 =−16.7° (CH3OH, c=1). MS (ES+, m/z): 537 ([M+Na]+, 100%); IR(KBr): 3310 (broad), 3049, 2974, 2934, 2875, 1644, 1604, 1545, 1501, 1457, 1420, 1371, 1346, 1219, 1155, 1104, 1065, 1045, 1018, 970, 944, 837, 814, 742, 718, 700, 565.

Provenance & Evidence