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 394399Notes

Reaction equation

HRID 394399 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:21]([C:23]2[S:27][C:26]([C:28]3[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=3)=[N:25][C:24]=2[CH3:38])O)[CH2:20][CH2:19]1.C(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][CH:21]([CH:18]2[CH2:19][CH2:20]2)[C:23]2[S:27][C:26]([C:28]3[CH:29]=[CH:30][C:31]([C:34]([F:36])([F:37])[F:35])=[CH:32][CH:33]=3)=[N:25][C:24]=2[CH3:38])=[CH:11][C:10]=1[CH3:16])[CH2:6][CH3:7])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22647406[Rac]-cyclopropyl-[4-methyl-2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanolHCID 23074534HCID 23074534, 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-(4-hydroxy-2-methyl-benzyl)-butyric acid ethyl ester (example 125 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 light yellow liquid.

Sources & evidence

ORD record
ord-6f1e4201c5104c11a61a2686750a2f96
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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