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

HRID 394291Notes

Reaction equation

HRID 394291 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].[Cl:19][C:20]1[CH:21]=[C:22]([C:27]2[S:28][C:29]([CH2:33]O)=[C:30]([CH3:32])[N:31]=2)[CH:23]=[CH:24][C:25]=1[F:26].ClC1C=C(C=CC=1F)C(N)=S.ClC(C(C)=O)C(OCC)=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][CH2:33][C:29]2[S:28][C:27]([C:22]3[CH:23]=[CH:24][C:25]([F:26])=[C:20]([Cl:19])[CH:21]=3)=[N:31][C:30]=2[CH3:32])=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

7

Reactant 6

HCID 11776TriphenylphosphineHCID 11858Ethyl 2-chloroacetoacetateHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 27795213-Chloro-4-fluorothiobenzamideHCID 226474712-(3-Chloro-4-fluorophenyl)-4-methyl-5-thiazolemethanolHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 68615972[Rac]-3-{4-[2-(3-chloro-4-fluoro-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-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 [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.

Sources & evidence

ORD record
ord-c80641efb12b49b5b8815d7fc71b0911
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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