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

HRID 394315

Reaktionsgleichung

Reaktionsgleichung von HRID 394315
[CH2:1]([O:3][C:4](=[O:19])[CH:5]([O:15][CH:16]([CH3:18])[CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([F:14])[CH:8]=1)[CH3:2].[F:20][C:21]([F:37])([F:36])[C:22]1[CH:27]=[CH:26][C:25]([C:28]2[S:29][CH:30]=[C:31]([CH2:33][CH2:34]O)[N:32]=2)=[CH:24][CH:23]=1.ClCC1N=C(C2C=CC(C(F)(F)F)=CC=2)SC=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:19])[CH:5]([O:15][CH:16]([CH3:18])[CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:34][CH2:33][C:31]2[N:32]=[C:28]([C:25]3[CH:24]=[CH:23][C:22]([C:21]([F:37])([F:20])[F:36])=[CH:27][CH:26]=3)[S:29][CH:30]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Komponenten

7

Edukt 5

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27366254-(Chloromethyl)-2-[4-(trifluoromethyl)phenyl]-1,3-thiazoleHCID 106122852-[2-(4-Trifluoromethyl-phenyl)-thiazol-4-yl]-ethanolHCID 68616202[Rac]-3-(3-fluoro-4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl ester

Produkt 1

HCID 68616676[Rac]-3-(3-fluoro-4-{2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 1 d], [rac]-3-(3-fluoro-4-hydroxy-phenyl)-2-isopropoxy-propionic acid ethyl ester [example 54 c]) was reacted with 2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethanol (prepared from 4-chloromethyl-2-(4-trifluoromethyl-phenyl)-thiazole (example 18 a]and 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-(3-fluoro-4-{2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-3-(3-fluoro-4-{2-[2-(4-trifluoromethyl-phenyl)-thiazol-4-yl]-ethoxy}-phenyl)-2-isopropoxy-propionic acid as colorless solid.

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-d3bba6d7669c4a46a6ae9add48d600e5
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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