Triphenylphosphine → [Rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid methyl ester

HRID 479165

Reaktionsgleichung

Reaktionsgleichung von HRID 479165
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]([OH:15])=[CH:8][CH:7]=1.[CH:20]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]([CH3:38])=[C:33]([CH2:35][CH2:36]O)[N:34]=2)=[CH:26][CH:25]=1)([CH3:22])[CH3:21].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:11]2[S:12][CH:13]=[CH:14][C:10]=2[C:9]([O:15][CH2:36][CH2:35][C:33]2[N:34]=[C:30]([C:27]3[CH:28]=[CH:29][C:24]([O:23][CH:20]([CH3:21])[CH3:22])=[CH:25][CH:26]=3)[O:31][C:32]=2[CH3:38])=[CH:8][CH:7]=1

Komponenten

5

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 180035882-[2-(4-Isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethanolHCID 68616873[Rac]-2-ethoxy-3-(4-hydroxy-benzo[b]thiophen-7-yl)-propionic acid methyl ester

Produkt 1

HCID 69557633[Rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid methyl ester

Versuchsvorschrift

In analogy to the procedure described in example 17 a], [rac]-2-ethoxy-3-(4-hydroxy-benzo[b]thiophen-7-yl)-propionic acid methyl ester was reacted with 2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethanol [PCT Int. Appl. (2000), WO0008002A1] in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid as light yellow amorphous solid.

Quellen und Nachweise

ORD-Eintrag
ord-67d03af7b80742bcaaadafdf40f5bccc
Quelldatensatz
uspto-grants-2003_11
Patentnummer
US06642389B2

Verknüpfte Notizen

Wird geladen…