Methanol → hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid methyl ester

HRID 1433210Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1433210
CS[C:3](SC)(SC)[CH:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:14]=2[CH:13]=1)[OH:5].[CH3:37][OH:38].[OH2:39]>>[CH3:37][O:38][C:3](=[O:39])[CH:4]([OH:5])[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[C:12]1[CH:32]=[CH:31][C:15]2[NH:16][C:17]([CH2:19][O:20][C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[N:18][C:14]=2[CH:13]=1

Komponenten

4

Edukt 3

HCID 887MethanolHCID 962WaterHCID 178504086HCID 178504086, Verbindung

Produkt 1

HCID 178501756hydroxy-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-acetic acid methyl esterAusbeute 78 %

Versuchsvorschrift

To a solution of 2,2,2-tris-methylsulfanyl-1-{2-[2-(4-trifluoromethyl-phenoxymethyl)-1H-benzoimidazol-5-yl]-phenyl}-ethanol (0.482 g, 0.875 mmol) in a mixed solvent (16 mL, MeOH: H2O=9:1) at rt was added mercuric chloride (0.855 g, 3.15 mmol) and mercuric oxide (0.303 g, 1.40 mmol). The reaction mixture was stirred for 12 hours. The solid was removed by filtration, and the collected filtrate was concentrated under reduced pressure. The residue was purified by chromatography (silica, hexanes: EtOAc, 1:1) to afford the title compound as a white solid (0.312 g, 78%). 1H NMR (400 MHz, CD3OD) δ (ppm): 7.71 (s, 1H), 7.62 (d, 2H, J=8.4 Hz), 7.50-7.46 (m, 1H), 7.7.41-7.36 (m, 2H), 7.34-7.31 (m, 2H), 7.25 (d, 2H, J=8.8 Hz), 5.49 (s, 2H), 5.27 (s, 1H), 3.62 (s, 3H). Mass Spectrum (LCMS, ESI pos.) Calcd. For C24H20F3N2O4: 457.4 (M+H), Found 457.3.

Aufarbeitung

  1. customThe solid was removed by filtration
  2. concentrationthe collected filtrate was concentrated under reduced pressure
  3. customThe residue was purified by chromatography (silica, hexanes: EtOAc, 1:1)

Quellen und Nachweise

ORD-Eintrag
ord-560c68f1342d467c861c629394d1c8da
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07612211B2

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