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

HRID 394324

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])[CH3:2].[CH3:19][C:20]1[N:21]=[C:22]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[S:23][C:24]=1[CH2:25]O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>>[CH2:1]([O:3][C:4](=[O:18])[CH:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:25][C:24]2[S:23][C:22]([C:27]3[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=3)=[N:21][C:20]=2[CH3:19])=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

Reactant 4

HCID 11776Triphenylphosphine

HCID 220568ethyl N-ethoxycarbonyliminocarbamate

HCID 736541(4-Methyl-2-phenyl-thiazol-5-yl)-methanol

HCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616822[Rac]-2-ethoxy-3-[2-methyl-4-(4-methyl-2-phenyl-thiazol-5-ylmethoxy)-phenyl]-propionic acid ethyl ester

Procedure

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 (4-methyl-2-phenyl-thiazol-5-yl)-methanol [PCT Int. Appl. (2002), WO 02/80899 A1] in the presence of triphenylphosphine and diethyl azodicarboxylate to yield [rac]-2-ethoxy-3-[2-methyl-4-(4-methyl-2-phenyl-thiazol-5-ylmethoxy)-phenyl]-propionic acid ethyl ester as colorless oil.

Sources & evidence

ORD record: ord-248e106c4cc845529222a04383df4c47
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Linked notes

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