Methyl acetoacetate → Methyl (+/-)-(E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-5-hydroxy-3-oxo-6-heptenoate

HRID 892957

Reaktionsgleichung

Reaktionsgleichung von HRID 892957
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:24]([CH3:26])[CH3:25])[N:11](/[CH:20]=[CH:21]/[CH:22]=[O:23])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:27]([O:33][CH3:34])(=[O:32])[CH2:28][C:29]([CH3:31])=[O:30].[H-].[Na+].C([Li])CCC>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([CH:24]([CH3:26])[CH3:25])[N:11](/[CH:20]=[CH:21]/[CH:22]([OH:23])[CH2:31][C:29](=[O:30])[CH2:28][C:27]([O:33][CH3:34])=[O:32])[C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Komponenten

5

Edukt 4

HCID 7757Methyl acetoacetateHCID 24758Sodium hydrideHCID 14849786(E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenalHCID 178418339Butyllithium

Produkt 1

HCID 14849790Methyl (+/-)-(E)-7-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-5-hydroxy-3-oxo-6-heptenoate

Versuchsvorschrift

From (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-1-yl]-2-propenal (0.100 g), methyl acetoacetate (0.028 ml), sodium hydride (0.031 g, washed with dry THF(3×3 ml)) and n-butyl lithium (1.4M in, hexanes, 0.26 ml) by the process as described for the preparation of Intermediate (10a) to afford a dark orange oil which was purified by FCC eluting with System A (2:3, 1:1) to afford the title compound (0.054 g) as an orange solid, Rf (System A 2:3) 0.18;

Aufarbeitung

  1. customto afford a dark orange oil which
  2. customwas purified by FCC
  3. washeluting with System A (2:3, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-d865bff12ac247fcb49cb52f6a89ec1b
Quelldatensatz
uspto-grants-1992_06
Patentnummer
US05120848

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