Triphenylphosphine → [Rac]-3-{4-[2-(2-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-4-yl)-ethoxy]-3-fluoro-phenyl)-2-ethoxy-propionic acid ethyl ester

HRID 394304

Reaktionsgleichung

Reaktionsgleichung von HRID 394304
[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].[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([C:28]3[S:29][C:30]([CH3:36])=[C:31]([CH2:33][CH2:34]O)[N:32]=3)=[CH:27][C:22]=2[O:21][CH2:20]1.COC(=O)CC(=O)C(Br)C.O1C2C=CC(C(=S)N)=CC=2OC1.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][CH2:34][CH2:33][C:31]2[N:32]=[C:28]([C:26]3[CH:25]=[CH:24][C:23]4[O:19][CH2:20][O:21][C:22]=4[CH:27]=3)[S:29][C:30]=2[CH3:36])=[C:9]([F:14])[CH:8]=1)[CH3:2]

Komponenten

8

Edukt 6

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27761262H-1,3-benzodioxole-5-carbothioamideHCID 9815681Methyl 4-bromo-3-oxopentanoateHCID 226474502-(2-Benzo[1,3]dioxol-5-yl-5-methyl-thiazol-4-yl)-ethanolHCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 68616319[Rac]-3-{4-[2-(2-benzo[1,3]dioxol-5-yl-5-methyl-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-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-4-yl)-ethanol (prepared from [rac]-4-bromo-3-oxo-pentanoic acid methyl ester [PCT Int. Appl. (2001), WO 01/792023 and benzo[1,3]dioxole-5-carbothioic acid amide in analogy to the procedures described in examples 12 a] and 12 b]) in tetrahydrofuran in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-3-{4-[2-(2-benzo[1,3]dioxol-5-yl-5-methyl-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-benzo[1,3]dioxol-5-yl-5-methyl-thiazol-4-yl)-ethoxy]-3-fluoro-phenyl}-2-ethoxy-propionic acid as colorless solid.

Aufarbeitung

  1. customdescribed in example 1 d

Quellen und Nachweise

ORD-Eintrag
ord-d1f80b95aac74c53ac5ab788880095e2
Quelldatensatz
uspto-grants-2004_10
Patentnummer
US06809110B2

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