Triphenylphosphine → [Rac]-2-ethoxy-3-{4-[2-(3-methoxy-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid ethyl ester
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].[CH3:19][O:20][C:21]1[CH:22]=[C:23]([C:27]2[S:28][C:29]([CH2:33]O)=[C:30]([CH3:32])[N:31]=2)[CH:24]=[CH:25][CH:26]=1.COC1C=C(C=CC=1)C(N)=S.ClC(C(C)=O)C(OCC)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)(C)C)=O)=NC(OC(C)(C)C)=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][C:29]2[S:28][C:27]([C:23]3[CH:24]=[CH:25][CH:26]=[C:21]([O:20][CH3:19])[CH:22]=3)=[N:31][C:30]=2[CH3:32])=[CH:9][C:8]=1[CH3:14])[CH3:2]Participants
7
Reactant 6
Product 1
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-(3-methoxy-phenyl)-4-methyl-thiazol-5-yl]-methanol (prepared from 3-methoxy-thiobenzamide [PCT Int. Appl. (2002), WO 0100433 A1] and ethyl 2-chloro-acetoacetate in analogy to the procedures described in example 33 a] and 33 b]) in the presence of triphenylphosphine and di-tert-butyl azodicarboxylate to yield [rac]-2-ethoxy-3-{4-[2-(3-methoxy-phenyl)-4-methyl-thiazol-5-ylmethoxy]-2-methyl-phenyl}-propionic acid ethyl ester as light yellow solid.
Sources & evidence
- ORD record
- ord-3e01de9fb3da49ec90d229e35a56c44d
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809110B2
Reaction notes
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