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HuagongsheHuagongshe Chemie-Druckbericht · Nur für Forschungszwecke
HRID 394304Erstellt: 23. Oktober 2026

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

https://huagongshe.com/de/reaction/394304

Reaktionsgleichung

Beteiligte Stoffe

RolleNameHCIDEinwaage
EduktTriphenylphosphineHCID 11776—
Eduktethyl N-ethoxycarbonyliminocarbamateHCID 220568—
Edukt2H-1,3-benzodioxole-5-carbothioamideHCID 2776126—
EduktMethyl 4-bromo-3-oxopentanoateHCID 9815681—
Edukt2-(2-Benzo[1,3]dioxol-5-yl-5-methyl-thiazol-4-yl)-ethanolHCID 22647450—
Edukt[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl esterHCID 68618019—
LösungsmittelTetrahydrofuranHCID 8028—
Produkt[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 esterHCID 68616319—

Reaktionsschritte

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.

Herkunft & Nachweise

DOI10.6084/m9.figshare.5104873.v1
PatentnummerUS06809110B2
Quelldatensatzuspto-grants-2004_10
ORD IDord-d1f80b95aac74c53ac5ab788880095e2
Quellennotizuspto-grants-2004_10