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

HRID 1433210ノート

反応式

HRID 1433210 の反応式
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

参加物

4

反応物 3

HCID 887MethanolHCID 962WaterHCID 178504086HCID 178504086、化合物

生成物 1

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

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-560c68f1342d467c861c629394d1c8da
出典データセット
uspto-grants-2009_11
特許番号
US07612211B2

反応ノート

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