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

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
Reactant	2-[2-(4-Isopropoxyphenyl)-5-methyl-1,3-oxazol-4-yl]ethanol	HCID 18003588	—
Reactant	[Rac]-2-ethoxy-3-(4-hydroxy-benzo[b]thiophen-7-yl)-propionic acid methyl ester	HCID 68616873	—
Product	[Rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid methyl ester	HCID 69557633	—

Reaction Steps

In analogy to the procedure described in example 17 a], [rac]-2-ethoxy-3-(4-hydroxy-benzo[b]thiophen-7-yl)-propionic acid methyl ester was reacted with 2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethanol [PCT Int. Appl. (2000), WO0008002A1] in the presence of triphenylphosphine and DEAD (diethyl azodicarboxylate) to yield [rac]-2-ethoxy-3-(4-{2-[2-(4-isopropoxy-phenyl)-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-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-(4-{2-[2-(4-isopropoxy-phenyl-5-methyl-oxazol-4-yl]-ethoxy}-benzo[b]thiophen-7-yl)-propionic acid as light yellow amorphous solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06642389B2
Source dataset	uspto-grants-2003_11
ORD ID	ord-67d03af7b80742bcaaadafdf40f5bccc
Source note	uspto-grants-2003_11