Fluoride Ion → 1-[(2'-Carbomethoxybiphenyl-4-yl)methyl]-4-chloro-5-hydroxymethyl-2-(cis-pent-1-en-1-yl)imidazole

HRID 465847

Reaktionsgleichung

Reaktionsgleichung von HRID 465847
[Si]([O:8][CH2:9][C:10]1[N:14]([CH2:15][C:16]2[CH:21]=[CH:20][C:19]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[C:28]([O:30][CH3:31])=[O:29])=[CH:18][CH:17]=2)[C:13](/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH3:36])=[N:12][C:11]=1[Cl:37])(C(C)(C)C)(C)C.[F-]>CCCCCC.C(OCC)(=O)C>[C:28]([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:19]1[CH:20]=[CH:21][C:16]([CH2:15][N:14]2[C:10]([CH2:9][OH:8])=[C:11]([Cl:37])[N:12]=[C:13]2/[CH:32]=[CH:33]\[CH2:34][CH2:35][CH3:36])=[CH:17][CH:18]=1)([O:30][CH3:31])=[O:29]

Komponenten

4

Versuchsvorschrift

5-t-Butyldimethylsilyloxymethyl-1-[(2'-carbomethoxybiphenyl-4-yl)methyl]-4-chloro-2-(cis-pent-1-en-1-yl)imidazole (100 mg) was desilylated with fluoride by procedures familiar to one skilled in the art. Flash chromatography in 1:1 hexane/ethyl acetate yielded 65 mg of a viscous, colorless oil. NMR (200 MHz, CDCl3) δ7.85 (d, 1H), 7.55 (t, 1H), 7.42 (t, 1H), 7.28 (m, 3H), 7.05 (d, 2H), 6.11 (d, 1H), 5.92 (d of t, 1H), 5.30 (s, 2H), 4.57 (d, 2H), 3.64 (s, 3H), 2.69 (quart., 2H), 1.62 (t, 1H), 1.47 (sext., 2H), 0.92 (t, 1H).

Quellen und Nachweise

ORD-Eintrag
ord-cb8e349a04034706a640c4e6286aeb06
Quelldatensatz
uspto-grants-1992_10
Patentnummer
US05153197

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