Triphenylphosphine → [Rac]-2-ethoxy-3-{3-fluoro-4-[3-(2-phenyl-thiazol-4-yl)-propoxy]-phenyl}-propionic acid ethyl ester

HRID 394277

Reaktionsgleichung

Reaktionsgleichung von HRID 394277
[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]([F:14])[CH:8]=1)[CH3:2].[C:19]1([C:25]2[S:26][CH:27]=[C:28]([CH2:30][CH2:31][CH2:32]O)[N:29]=2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[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][CH2:32][CH2:31][CH2:30][C:28]2[N:29]=[C:25]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[S:26][CH:27]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 226474953-(2-Phenyl-thiazol-4-yl)-propan-1-olHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 68617998[Rac]-2-ethoxy-3-{3-fluoro-4-[3-(2-phenyl-thiazol-4-yl)-propoxy]-phenyl}-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

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 3-(2-phenyl-thiazol-4-yl)-propan-1-ol in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-{3-fluoro-4-[3-(2-phenyl-thiazol-4-yl)-propoxy]-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-[3-(2-phenyl-thiazol-4-yl)-propoxy]-phenyl}-propionic acid as a colorless gum.

Aufarbeitung

  1. customdescribed in example 1 d

Quellen und Nachweise

ORD-Eintrag
ord-1931ec9b7dde4fa6bd9521b8a5014b4d
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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