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

HRID 394407Notes

Reaction equation

HRID 394407 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4](OCCCC)[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[CH3:13].[CH:20]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)[CH2:22][CH2:21]1.[CH2:41](P(CCCC)CCCC)[CH2:42]CC.[CH3:54]N(C)C(N=NC(N(C)C)=O)=O>>[CH2:1]([O:2][C:3](=[O:19])[CH:4]([CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH:23]([CH:20]2[CH2:22][CH2:21]2)[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])=[CH:8][C:7]=1[CH3:13])[CH2:41][CH3:42])[CH3:54]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22647406[Rac]-cyclopropyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanolHCID 68616878HCID 68616878, compound

Product 1

HCID 686166872-(4-{Cyclopropyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methoxy}-2-methyl-benzyl)-butyric acid ethyl ester

Procedure

In analogy to the procedure described in example 10 c], [rac]-2-butoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (example 131 c]) was reacted with [rac]-cyclopropyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol (example 121 a]) in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield 2-(4-{cyclopropyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methoxy}-2-methyl-benzyl)-butyric acid ethyl ester as a mixture of two diastereomeric racemates as yellow liquid.

Sources & evidence

ORD record
ord-dabf3c683ca34517a6da94d6cba2283c
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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