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

HRID 854572

Reaction equation

HRID 854572 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

HCID 694708723-{4-[4-Isopropyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxymethyl]-2-methyl-phenyl}-propionic acid methyl esterYield 62.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-4aba11daedae42cda1a16f8c20d5eaa3
Source dataset
uspto-grants-2007_08
Patent number
US07259175B2

Linked notes

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