Sodium hydride → HCID 69557720, Verbindung

HRID 479222

Reaktionsgleichung

Reaktionsgleichung von HRID 479222
[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]([CH3:14])[CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:24][CH:25]=1.[H-].[Na+]>CN(C)C=O>[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][CH:29]=[CH:30][CH:31]=3)[O:24][CH:25]=2)=[C:9]([CH3:14])[CH:8]=1)[CH3:2]

Komponenten

5

Edukt 3

HCID 24758Sodium hydrideHCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazoleHCID 22708451Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoate

Produkt 1

HCID 69557720HCID 69557720, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 108 c], [rac]-2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid ethyl ester [PCT Int. Appl. (2001), WO01/40172A1] was treated with 4-chloromethyl-2-phenyl-oxazole [prepared from benzamide and 1,3-dichloroacetone as described in Bioorg. Med. Chem. Lett. (2000), 10(17), 2041-2044] and sodium hydride in N,N-dimethylformamide to yield [rac]-2-ethoxy-3-[3-methyl-4-(2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-ethoxy-3-[3-methyl-4-(2-phenyl-oxazol-4-ylmethoxy) -phenyl]-propionic acid as colorless gum.

Quellen und Nachweise

ORD-Eintrag
ord-4519f382f92446308bce4d7c54e5de22
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

Verknüpfte Notizen

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