Potassium Iodide → HCID 68616040, compound

HRID 394309

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])=[C:9]([F:14])[CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=2)[S:24][CH:25]=1.CC1C=CC=CC=1C(N)=S.ClCC(CCl)=O.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[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][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=3)[S:24][CH:25]=2)=[C:9]([F:14])[CH:8]=1)[CH3:2]

Participants

Reactant 6

HCID 4875Potassium Iodide

HCID 107931,3-Dichloroacetone

HCID 10796Cesium carbonate

HCID 8168102-Methylbenzenecarbothioamide

HCID 20635964-(Chloromethyl)-2-(4-methylphenyl)-1,3-thiazole

HCID 68618019[Rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616040HCID 68616040, compound

Procedure

In analogy to the procedure described in example 14 b], [rac]-2-ethoxy-3-(3-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (example 7 a]) was reacted with 4-chloromethyl-2-p-tolyl-thiazole (prepared from 4 methyl-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) in the presence of cesium carbonate and potassium iodide to yield [rac]-2-ethoxy-3-[3-fluoro-4-(2-p-tolyl-thiazol-4-ylmethoxy)-phenyl]-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 4 e], to yield [rac]-2-ethoxy-3-[3-fluoro-4-(2-p-tolyl-thiazol-4-ylmethoxy)-phenyl]-propionic acid as light yellow solid.

Sources & evidence

ORD record: ord-44b43c66bbdf4c568def9ef9250446cb
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809110B2

Linked notes

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