Reaktionsgleichung
C(OC(=O)C(OCC)CC1C=CC(O)=C(F)C=1)C.[CH3:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][CH:29]=[C:30]([CH2:32]CO)[N:31]=2)=[CH:23][CH:22]=1.COC1C=CC(C(N)=S)=CC=1.[Cl:46]CC(CCl)=O>>[Cl:46][CH2:32][C:30]1[N:31]=[C:27]([C:24]2[CH:25]=[CH:26][C:21]([O:20][CH3:19])=[CH:22][CH:23]=2)[S:28][CH:29]=1Komponenten
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-(4-methoxy-phenyl)-thiazol-4-yl]-ethanol (prepared from 4-methoxy-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a] to yield 4-chloromethyl-2-(4-methoxy-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-(4-methoxy-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-(4-methoxy-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-propionic acid as a light yellow solid.
Aufarbeitung
- customdescribed in example 1 d
Quellen und Nachweise
- ORD-Eintrag
- ord-825811ae42494de6a564590b8aac7e92
- Quelldatensatz
- uspto-grants-2004_10
- Patentnummer
- US06809110B2
Verknüpfte Notizen
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