Triphenylphosphine → [Rac]-2-ethoxy-3-(7-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-4-yl)-propionic acid methyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
Reactant	[Rac]-2-ethoxy-3-(4-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy-}-benzo[b]thiophen-7-yl)-propionic acid	HCID 18003586	—
Reactant	[Rac]-2-ethoxy-3-(7-hydroxy-benzo[b]thiophen-4-yl)-propionic acid methyl ester	HCID 68616696	—
Product	[Rac]-2-ethoxy-3-(7-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-4-yl)-propionic acid methyl ester	HCID 69556958	—

Reaction Steps

In analogy to the procedure described in example 17 a], [rac]-2-ethoxy-3-(7-hydroxy-benzo[b]thiophen-4-yl)-propionic acid methyl ester (example 151 a]) was reacted with 2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethanol (example 95) in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-(7-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-4-yl)-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 91 e] to yield [rac]-2-ethoxy-3-(7-{2-[2-(2-ethoxy-4-fluoro-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-4-yl)-propionic acid as colorless solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06642389B2
Source dataset	uspto-grants-2003_11
ORD ID	ord-9620b04b20fd4207b8ded4b3bd5b2210
Source note	uspto-grants-2003_11