N,N,N',N'-Tetramethylazodicarboxamide → [Rac]-2-ethoxy-3-[2-methyl-4-[2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester

HRID 394367Notes

Reaction equation

HRID 394367 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])=[CH:9][C:8]=1[CH3:14])[CH3:2].[F:19][C:20]([F:35])([F:34])[C:21]1[CH:26]=[CH:25][C:24]([C:27]2[S:28][C:29]([CH2:32]O)=[CH:30][N:31]=2)=[CH:23][CH:22]=1.C(P(CCCC)CCCC)CCC.CN(C)C(N=NC(N(C)C)=O)=O>>[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][CH2:32][C:29]2[S:28][C:27]([C:24]3[CH:23]=[CH:22][C:21]([C:20]([F:35])([F:19])[F:34])=[CH:26][CH:25]=3)=[N:31][CH:30]=2)=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22647407{2-[4-(Trifluoromethyl)phenyl]-1,3-thiazol-5-yl}methanolHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616655[Rac]-2-ethoxy-3-[2-methyl-4-[2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester

Procedure

In analogy to the procedure described in example 10 c], [rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 10 b]) was reacted with [2-(4-trifluoromethyl-phenyl)-thiazol-5-yl]-methanol [PCT Int. Appl. (2002), WO 02/062774 A1] in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield [rac]-2-ethoxy-3-{2-methyl-4-[2-(4-trifluoromethyl-phenyl)-thiazol-5-ylmethoxy]-phenyl}-propionic acid ethyl ester as yellow crystals.

Sources & evidence

ORD record
ord-d2bda2d1dc794dad879533fd65b75375
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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