1,3-Dichloroacetone → 4-(Chloromethyl)-2-phenyl-1,3-thiazole

HRID 394271

Reaktionsgleichung

Reaktionsgleichung von HRID 394271
C(OC(=O)C(OCC)CC1C=CC(O)=C(F)C=1)C.[C:19]1([C:25]2[S:26][CH:27]=[C:28]([CH2:30]CO)[N:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C(N)(=S)C1C=CC=CC=1.[Cl:42]CC(CCl)=O>>[Cl:42][CH2:30][C:28]1[N:29]=[C:25]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[S:26][CH:27]=1

Komponenten

5

Edukt 4

HCID 107931,3-DichloroacetoneHCID 683563ThiobenzamideHCID 106083152-Phenyl-4-(beta-hydroxyethyl)thiazoleHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 2369694-(Chloromethyl)-2-phenyl-1,3-thiazole

Versuchsvorschrift

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with 2-(2-phenyl-thiazol-4-yl)-ethanol (prepared from thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a] to give 4-chloromethyl-2-phenyl-thiazole followed by side chain elongation in analogy to the sequence described in examples 13 a] to 13 d]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]2-ethoxy-3-{3-fluoro-4-[2-(2-phenyl-thiazol-4-yl)-ethoxy]-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-(2-phenyl-thiazol-4-yl)-ethoxy]-phenyl}-propionic acid as a light yellow gum.

Aufarbeitung

  1. customdescribed in example 1 d

Quellen und Nachweise

ORD-Eintrag
ord-eaa609cebea543ea9fbd5923d28b44cf
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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