Sodium hydride → [Rac]-2-ethoxy-3-[7-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-4yl]-propionic acid methyl ester

HRID 479232

Reaktionsgleichung

Reaktionsgleichung von HRID 479232
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][S:11][C:10]=2[C:9]([OH:15])=[CH:8][CH:7]=1.Cl[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:25][C:26]=1[CH3:27].[H-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[CH:13]=[CH:12][S:11][C:10]=2[C:9]([O:15][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[O:25][C:26]=2[CH3:27])=[CH:8][CH:7]=1

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazoleHCID 68616696[Rac]-2-ethoxy-3-(7-hydroxy-benzo[b]thiophen-4-yl)-propionic acid methyl ester

Produkt 1

HCID 69557098[Rac]-2-ethoxy-3-[7-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-4yl]-propionic acid methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 108 c], [rac]-2-ethoxy-3-(7-hydroxy-benzo[b]thiophen-4-yl)-propionic acid methyl ester was treated with 4-chloromethyl-5-methyl-2-phenyloxazole and sodium hydride in N,N-dimethylformamide to yield [rac]-2-ethoxy-3-[7-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-4yl]-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-ethoxy-3-[7-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzo[b]thiophen-4-yl]-propionic acid as colorless solid.

Quellen und Nachweise

ORD-Eintrag
ord-0872a732faa5471bb2caf5a5986266d5
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

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