1,3-Dichloroacetone → [Rac]-2-ethoxy-3-{3-fluoro-4-[2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-phenyl}-propionic acid ethyl ester

HRID 394233

Reaktionsgleichung

Reaktionsgleichung von HRID 394233
[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)[S:24][CH:25]=1.FC(F)(F)C1C=CC(C(N)=S)=CC=1.ClCC(CCl)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:33])[F:34])=[CH:30][CH:31]=3)[S:24][CH:25]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Komponenten

7

Edukt 5

HCID 107931,3-DichloroacetoneHCID 10796Cesium carbonateHCID 27348234-(Trifluoromethyl)thiobenzamideHCID 27366254-(Chloromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 68629057[Rac]-2-ethoxy-3-{3-fluoro-4-[2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-phenyl}-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 4 d], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with 4-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (prepared from 4-trifluoromethyl-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) in acetonitrile in the presence of cesium carbonate to yield [rac]-2-ethoxy-3-{3-fluoro-4-[2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-phenyl}-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-2-ethoxy-3-{3-fluoro-4-[2-(4-trifluoromethyl-phenyl)-thiazol-4-ylmethoxy]-phenyl}-propionic acid as colorless solid.

Aufarbeitung

  1. customdescribed in example 4 d

Quellen und Nachweise

ORD-Eintrag
ord-8ddbd16497524a56a40230c052498602
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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