Triphenylphosphine → [Rac]-3-(4-{2-[2-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid ethyl ester

関与物質

役割	名称	HCID	仕込み量
反応物	Triphenylphosphine	HCID 11776	—
反応物	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
反応物	Methyl 4-bromo-3-oxopentanoate	HCID 9815681	—
反応物	2-[2-(3,5-Dimethylphenyl)-5-methyl-1,3-thiazol-4-yl]ethanol	HCID 22647410	—
反応物	3,5-Dimethylbenzene-1-carbothioamide	HCID 22647568	—
反応物	[Rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester	HCID 22708420	—
溶媒	Tetrahydrofuran	HCID 8028	—
生成物	[Rac]-3-(4-{2-[2-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid ethyl ester	HCID 68618347	—

反応手順

In analogy to the procedure described in example 1 d], [rac]-2-ethoxy-3-(4-hydroxy-3-methoxy-phenyl)-propionic acid ethyl ester [example 48 a)] was reacted with 2-[2-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethanol (prepared from [rac]-4-bromo-3-oxo-pentanoic acid methyl ester [PCT Int. Appl. (2001), WO 01/79202] and 3,5-dimethyl-thiobenzamide (from 3,5-dimethyl-benzonitrile and NaSH, NH4Cl in N,N-dimethylformamide) 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-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-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-(3,5-dimethyl-phenyl)-5-methyl-thiazol-4-yl]-ethoxy}-3-methoxy-phenyl)-2-ethoxy-propionic acid as colorless solid.

情報源と証拠

DOI	10.6084/m9.figshare.5104873.v1
特許番号	US06809110B2
出典データセット	uspto-grants-2004_10
ORD ID	ord-b090c8feed2e4c309cf99b2518ed673b
出典メモ	uspto-grants-2004_10