Potassium Iodide → [Rac]-2-butoxy-3-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester

HRID 394405Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].Cl[CH2:21][C:22]1[S:26][C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]([F:36])([F:35])[F:34])=[CH:29][CH:28]=2)=[N:24][C:23]=1[CH3:37].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:14][CH2:15][CH2:16][CH2:17][CH3:18])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:21][C:22]2[S:26][C:25]([C:27]3[CH:28]=[CH:29][C:30]([C:33]([F:36])([F:34])[F:35])=[CH:31][CH:32]=3)=[N:24][C:23]=2[CH3:37])=[CH:8][C:7]=1[CH3:13]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 10796Cesium carbonate

HCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole

HCID 68616878HCID 68616878, compound

Product 1

HCID 68617854[Rac]-2-butoxy-3-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester

Procedure

In analogy to the procedure described in example 14 b], [rac]-2-butoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester was reacted with 5-chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazole [PCT Int. Appl. (2002), WO 0292590 A1] in the presence of cesium carbonate and potassium iodide to yield [rac]-2-butoxy-3-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid methyl ester as colorless liquid.

Sources & evidence

ORD record: ord-1393efce1ad6494fb861c19793793516
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Reaction notes

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