Water → 3-{4-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-methyl-phenyl}-propionic acid methyl ester

HRID 854572

Reaktionsgleichung

Reaktionsgleichung von HRID 854572
[CH:1]([C:4]1[N:5]=[C:6]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][CH:12]=2)[S:7][C:8]=1[CH2:9][OH:10])([CH3:3])[CH3:2].[CH3:21][O:22][C:23](=[O:35])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32]I)=[CH:28][C:27]=1[CH3:34].[H-].[Na+].O>CN(C=O)C>[CH3:21][O:22][C:23](=[O:35])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([CH2:32][O:10][CH2:9][C:8]2[S:7][C:6]([C:11]3[CH:16]=[CH:15][C:14]([C:17]([F:19])([F:20])[F:18])=[CH:13][CH:12]=3)=[N:5][C:4]=2[CH:1]([CH3:3])[CH3:2])=[CH:28][C:27]=1[CH3:34]

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 574319743-(4-Iodomethyl-2-methyl-phenyl)-propionic acid methyl esterHCID 587657624-Isopropyl-2-[4-(trifluoromethyl)phenyl]thiazole-5-methanol

Produkt 1

HCID 694708723-{4-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-methyl-phenyl}-propionic acid methyl esterAusbeute 62,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of [4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (0.056 g, 0.18 mmol) and 3-(4-Iodomethyl-2-methyl-phenyl)-propionic acid methyl ester (0.070 g, 0.22 mol) in DMF (1 mL) is added sodium hydride (60% dispersion, 0.016 g, 0.67 mmol). After 3.5 h, water is added, and the mixture is extracted with EtOAc. The organics are dried with MgSO4 and concentrated. The crude material is purified by flash chromatography to yield the title compound (55 mg, 60%).

Aufarbeitung

  1. extractionthe mixture is extracted with EtOAc
  2. dry with materialThe organics are dried with MgSO4
  3. concentrationconcentrated
  4. customThe crude material is purified by flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-4aba11daedae42cda1a16f8c20d5eaa3
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259175B2

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