Triphenylphosphine → [Rac]-3-{4-[2-(3-chloro-4-fluoro-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Ethyl 2-chloroacetoacetate	HCID 11858	—
Reactant	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
Reactant	3-Chloro-4-fluorothiobenzamide	HCID 2779521	—
Reactant	2-(3-Chloro-4-fluorophenyl)-4-methyl-5-thiazolemethanol	HCID 22647471	—
Reactant	[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester	HCID 57792490	—
Product	[Rac]-3-{4-[2-(3-chloro-4-fluoro-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester	HCID 68615972	—

Reaction Steps

In analogy to the procedure described in example 10 c], [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 10 b]) was reacted with [2-(3-chloro-4-fluoro-phenyl)-4-methyl-thiazol-5-yl)-methanol (prepared from 3-chloro-4-fluoro-thiobenzamide and ethyl 2-chloro-acetoacetate in analogy to the procedures described in examples 33 a] and 33 b]) in the presence of triphenylphosphine and diethyl azodicarboxylate to yield [rac]-3-{4-[2-(3-chloro-4-fluoro-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid ethyl ester as light yellow liquid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06809110B2
Source dataset	uspto-grants-2004_10
ORD ID	ord-c80641efb12b49b5b8815d7fc71b0911
Source note	uspto-grants-2004_10