Potassium Iodide → (S)-2-ethoxy-3-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-2-trifluoromethyl-phenyl]-propionic acid methyl ester

HRID 1064953Notes

Reaction equation

HRID 1064953 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([O:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[C:13]([F:16])([F:15])[F:14].Cl[CH2:22][C:23]1[N:24]=[C:25]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=2)[O:26][C:27]=1[CH3:28].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:20])[C@@H:4]([O:17][CH2:18][CH3:19])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:22][C:23]2[N:24]=[C:25]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[O:26][C:27]=2[CH3:28])=[CH:8][C:7]=1[C:13]([F:16])([F:14])[F:15]

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 69280496(2S)-2-ethoxy-3-(4-hydroxy-2-trifluoromethyl-phenyl)-propionic acid methyl ester

Product 1

HCID 69279917(S)-2-ethoxy-3-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-2-trifluoromethyl-phenyl]-propionic acid methyl ester

Procedure

In analogy to the procedure described in example 1 f], (2S)-2-ethoxy-3-(4-hydroxy-2-trifluoromethyl-phenyl)-propionic acid methyl ester was reacted with 4-chloromethyl-5-methyl-2-phenyl-oxazole in the presence of cesium carbonate and potassium iodide to yield (S)-2-ethoxy-3-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-2-trifluoromethyl-phenyl]-propionic acid methyl ester as colorless liquid.

Sources & evidence

ORD record
ord-7ab89b37bb0a4917b05cdf264b886578
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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