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

HRID 1064955Notes

Reaction equation

HRID 1064955 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][C:30]=2[F:35])[O:26][C:27]=1[CH3:28].FC1C=CC=CC=1C=O.O=P(Cl)(Cl)Cl.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][C:30]=3[F:35])[O:26][C:27]=2[CH3:28])=[CH:8][C:7]=1[C:13]([F:16])([F:14])[F:15]

Participants

7

Reactant 6

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 24813Phosphorus oxychlorideHCID 67970o-FluorobenzaldehydeHCID 44411144-Chloromethyl-2-(2-fluoro-phenyl)-5-methyl-oxazoleHCID 69280496(2S)-2-ethoxy-3-(4-hydroxy-2-trifluoromethyl-phenyl)-propionic acid methyl ester

Product 1

HCID 69282252(S)-2-ethoxy-3-{4-[2-(2-fluoro-phenyl)-5-methyl-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 (example 21 f]) was reacted with with 4-chloromethyl-2-(2-fluoro-phenyl)-5-methyl-oxazole (prepared from 2-fluoro-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 5 a] and 2 b]) in the presence of cesium carbonate and potassium iodide to yield (S)-2-ethoxy-3-{4-[2-(2-fluoro-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-trifluoromethyl-phenyl}-propionic acid methyl ester as colorless solid.

Sources & evidence

ORD record
ord-aec1b62df26b4006837fff84c74a816f
Source dataset
uspto-grants-2005_11
Patent number
US06969725B2

Reaction notes

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