N,N,N',N'-Tetramethylazodicarboxamide → HCID 68616528, compound

HRID 394358Notes

Reaction equation

HRID 394358 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].[Cl:19][C:20]1[CH:25]=[CH:24][C:23]([C:26]2[S:27][C:28]([CH2:32][CH2:33]O)=[C:29]([CH3:31])[N:30]=2)=[CH:22][CH:21]=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][CH2:33][CH2:32][C:28]2[S:27][C:26]([C:23]3[CH:24]=[CH:25][C:20]([Cl:19])=[CH:21][CH:22]=3)=[N:30][C:29]=2[CH3:31])=[CH:9][C:8]=1[CH3:14])[CH3:2]

Participants

5

Reactant 4

HCID 4278N,N,N',N'-TetramethylazodicarboxamideHCID 13831TributylphosphineHCID 22647448HCID 22647448, compoundHCID 57792490[Rac]-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester

Product 1

HCID 68616528HCID 68616528, compound

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-[2-(4-chloro-phenyl)-4-methyl-thiazol-5-yl]-ethanol in the presence of tributylphosphine and N,N,N′,N′-tetramethyl azodicarboxamide to yield [rac]-3-(4-{2-[2-(4-chloro-phenyl)-4-methyl-thiazol-5-yl]-ethoxy}-2-methyl-phenyl)-2-ethoxy-propionic acid ethyl ester as colorless liquid.

Sources & evidence

ORD record
ord-a6517c577c3d4b92affb23b1d7c4630f
Source dataset
uspto-grants-2004_10
Patent number
US06809110B2

Reaction notes

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