Potassium Iodide → [Rac]-2-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzyl}-butyric acid ethyl ester

HRID 394392Notes

Reaction equation

HRID 394392 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])[CH2:6][CH3:7])[CH3:2].Cl[CH2:19][C:20]1[S:24][C:23]([C:25]2[CH:30]=[CH:29][C:28]([C:31]([F:34])([F:33])[F:32])=[CH:27][CH:26]=2)=[N:22][C:21]=1[CH3:35].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[S:24][C:23]([C:25]3[CH:26]=[CH:27][C:28]([C:31]([F:34])([F:32])[F:33])=[CH:29][CH:30]=3)=[N:22][C:21]=2[CH3:35])=[CH:11][C:10]=1[CH3:16])[CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 27830065-Chloromethyl-4-methyl-2-(4-trifluoromethyl-phenyl)-thiazoleHCID 23074534HCID 23074534, compound

Product 1

HCID 68617864[Rac]-2-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzyl}-butyric acid ethyl ester

Procedure

In analogy to the procedure described in example 14 b], [rac]-2-(4-hydroxy-2-methyl-benzyl)-butyric acid ethyl 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-{2-methyl-4-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-benzyl}-butyric acid ethyl ester as colorless oil.

Sources & evidence

ORD record
ord-51683f2ac1a6478dbc3743f4f48b0344
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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