N,N,N',N'-Tetramethylazodicarboxamide → [Rac]-2-(2-methyl-4-{1-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-benzyl)-butyric acid ethyl ester

HRID 394401Notes

Reaction equation

HRID 394401 reaction equation
[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])[CH2:6][CH3:7])[CH3:2].[CH:18]1([CH:23]([C:25]2[S:29][C:28]([C:30]3[CH:35]=[CH:34][C:33]([C:36]([F:39])([F:38])[F:37])=[CH:32][CH:31]=3)=[N:27][C:26]=2[CH3:40])O)CCCC1.[CH2:41](P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>>[CH2:1]([O:3][C:4](=[O:17])[CH:5]([CH2:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][C:23]([CH3:18])([C:25]2[S:29][C:28]([C:30]3[CH:31]=[CH:32][C:33]([C:36]([F:37])([F:38])[F:39])=[CH:34][CH:35]=3)=[N:27][C:26]=2[CH3:40])[CH3:41])=[CH:11][C:10]=1[CH3:16])[CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22647598[Rac]-cyclopentyl-(4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanolHCID 23074534HCID 23074534, compound

Product 1

HCID 68617029[Rac]-2-(2-methyl-4-{1-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-benzyl)-butyric acid ethyl ester

Procedure

In analogy to the procedure described in example 10 c], [rac]-2-(4-hydroxy-2-methyl-benzyl)-butyric acid ethyl ester (example 125 c]) was reacted with 2-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-propan-2-ol [PCT Int. Appl. (2002), WO 02/062774 A1] in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield [rac]-2-(2-methyl-4-{1-methyl-1-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-ethoxy}-benzyl)-butyric acid ethyl ester as colorless oil.

Sources & evidence

ORD record
ord-70944a3d1d9f4803970a84594e2550cd
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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