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

HRID 394249Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394249
[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[Cl:18][C:19]1[CH:20]=[C:21]([C:26]2[S:27][CH:28]=[C:29]([CH2:31]Cl)[N:30]=2)[CH:22]=[CH:23][C:24]=1[F:25].ClC1C=C(C=CC=1F)C(N)=S.ClCC(CCl)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:31][C:29]2[N:30]=[C:26]([C:21]3[CH:22]=[CH:23][C:24]([F:25])=[C:19]([Cl:18])[CH:20]=3)[S:27][CH:28]=2)=[CH:8][C:7]=1[CH3:13]

Komponenten

7

Edukt 6

HCID 4875Potassium IodideHCID 107931,3-DichloroacetoneHCID 10796Cesium carbonateHCID 27795213-Chloro-4-fluorothiobenzamideHCID 223401432-(3-Chloro-4-fluorophenyl)-4-(chloromethyl)-1,3-thiazoleHCID 68616579(S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 68615930(2S)-3-{4-[2-(3-chloro-4-fluoro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester

Versuchsvorschrift

In analogy to the procedure described in example 14 b], (2S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester was reacted with 2-(3-chloro-4-fluoro-phenyl)-4-chloromethyl-thiazole (prepared from 3-chloro-4-fluoro-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) in the presence of cesium carbonate and potassium iodide to yield (2S)-3-{4-[2-(3-chloro-4-fluoro-phenyl)-thiazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester as yellow liquid.

Quellen und Nachweise

ORD-Eintrag
ord-77f199fca5004090a57a7eb0f1c63618
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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