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

HRID 394279

Reaktionsgleichung

Reaktionsgleichung von HRID 394279
[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]([C:23]1[CH:28]=[CH:27][C:26]([C:29]2[S:30][CH:31]=[C:32]([CH2:34][CH2:35]O)[N:33]=2)=[CH:25][CH:24]=1)([CH3:22])([CH3:21])[CH3:20].C(C1C=CC(C2SC=C(CCl)N=2)=CC=1)(C)(C)C.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][CH2:35][CH2:34][C:32]2[N:33]=[C:29]([C:26]3[CH:27]=[CH:28][C:23]([C:19]([CH3:20])([CH3:22])[CH3:21])=[CH:24][CH:25]=3)[S:30][CH:31]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Komponenten

7

Edukt 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 223401634-Chloromethyl-2-(4-tert-butyl phenyl)thiazoleHCID 226475512-[2-(4-Tert-butyl-phenyl)-thiazol-4-yl]-ethanolHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 68618235[Rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-thiazol-4-yl]-ethoxy}-3-fluoro-phenyl)-2-ethoxy-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 2-[2-(4-tert-butyl-phenyl)-thiazol-4-yl]-ethanol (prepared from 2-(4-tert-butyl-phenyl)-4-chloromethyl-thiazole (example 4 a]) 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]-3-(4-{2-[2-(4-tert-butyl-phenyl)-thiazol-4-yl]-ethoxy}-3-fluoro-phenyl)-2-ethoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-3-(4-{2-[2-(4-tert-butyl-phenyl)-thiazol-4-yl]-ethoxy}-3-fluoro-phenyl)-2-ethoxy-propionic acid as a light yellow solid.

Aufarbeitung

  1. customdescribed in example 1 d
  2. customto 13 d

Quellen und Nachweise

ORD-Eintrag
ord-6692ac6ce34141fba21dfe84ef24f079
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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