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

HRID 1433210노트

반응식

HRID 1433210 반응식
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

참가 물질

4

반응물 3

HCID 887MethanolHCID 962WaterHCID 178504086HCID 178504086, 화합물

생성물 1

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

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-560c68f1342d467c861c629394d1c8da
출처 데이터셋
uspto-grants-2009_11
특허 번호
US07612211B2

반응 노트

불러오는 중…