Potassium Iodide → (2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-ethyl-phenyl}-2-ethoxy-propionic acid methyl ester

HRID 394267Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([O:15][CH2:16][CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH2:13][CH3:14].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:18])[C@@H:4]([O:15][CH2:16][CH3:17])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)=[CH:8][C:7]=1[CH2:13][CH3:14]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 10796Cesium carbonate

HCID 6102974-(Chloromethyl)-2-(4-chlorophenyl)-1,3-thiazole

HCID 68617384(2S)-2-ethoxy-3-(2-ethyl-4-hydroxy-phenyl)-propionic acid methyl ester

Product 1

HCID 68617881(2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-ethyl-phenyl}-2-ethoxy-propionic acid methyl ester

Procedure

In analogy to the procedure described in example 14 b], (2S)-2-ethoxy-3-(2-ethyl-4-hydroxy-phenyl)-propionic acid methyl ester was reacted with 4-chloromethyl-2-(4-chloro-phenyl)-thiazole (example 14 a]) in the presence of cesium carbonate and potassium iodide to yield (2S)-3-{4-[2-(4-chloro-phenyl)-thiazol-4-ylmethoxy]-2-ethyl-phenyl}-2-ethoxy-propionic acid methyl ester as colorless liquid.

Sources & evidence

ORD record: ord-51721e72d6214fb4b79a19612fb7328e
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Reaction notes

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