1,3-Dichloroacetone → [Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-propionic acid ethyl ester

HRID 394230

Reaction equation

HRID 394230 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]([CH3:14])[CH:8]=1)[CH3:2].Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][C:29]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=2)[S:24][CH:25]=1.C(C1C=CC(C(N)=S)=CC=1)(C)C.ClCC(CCl)=O.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[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]([CH:32]([CH3:34])[CH3:33])=[CH:28][CH:27]=3)[S:24][CH:25]=2)=[C:9]([CH3:14])[CH:8]=1)[CH3:2]

Participants

7

Reactant 5

HCID 107931,3-DichloroacetoneHCID 10796Cesium carbonateHCID 20788314-(Propan-2-yl)benzene-1-carbothioamideHCID 20956974-Chloromethyl-2-(4-isopropyl-phenyl)-thiazoleHCID 22708451Ethyl 2-ethoxy-3-(4-hydroxy-3-methylphenyl)propanoate

Product 1

HCID 68617181[Rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-propionic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

In analogy to the procedure described in example 4 d], [rac]-2-ethoxy-3-(4-hydroxy-3-methyl-phenyl)-propionic acid ethyl ester (example 4 c]) was reacted with 4-chloromethyl-2-(4-isopropyl-phenyl)-thiazole (prepared from 4-isopropyl-thiobenzamide and 1,3-dichloroacetone in analogy to the procedure described in example 4 a]) in acetonitrile in the presence of cesium carbonate to yield [rac]-2-ethoxy-3-{4-[2-(4-isopropyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-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-{4-[2-(4-isopropyl-phenyl)-thiazol-4-ylmethoxy]-3-methyl-phenyl}-propionic acid as colorless gum.

Workup

  1. customdescribed in example 4 d

Sources & evidence

ORD record
ord-9dd52754fb0f4d4aa8243b639a3606fa
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Linked notes

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