3-Fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde → [Rac]-2-ethoxy-3-{3-fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid
Reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[N:14]=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[O:16][C:17]=1[CH3:18])C=O.[Cl-].C([O:33][C:34]([CH:36]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:37][CH2:38][CH3:39])=[O:35])C1C=CC=CC=1.[Cl-].[CH2:60](OC(C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OC)=O)C1C=CC=CC=1>>[CH2:38]([O:37][CH:36]([CH2:60][C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH2:12][C:13]2[N:14]=[C:15]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[O:16][C:17]=2[CH3:18])=[C:2]([F:1])[CH:3]=1)[C:34]([OH:33])=[O:35])[CH3:39]Participants
Reactant 3
Product 1
Procedure
In analogy to the procedures described in examples 114 b], c] and d], 3-fluoro-4-hydroxy-benzaldehyde was reacted with methanesulfonic acid 2-(5-methyl-2-phenyl-oxazol-4-yl)-ethyl ester [PCT Int. Appl. (2000) WO0008002] to give 3-fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde. Treatment of 3-fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde with (benzyloxycarbonyl-ethoxy-methyl)-triphenyl-phosphonium chloride (prepared in analogy to the procedure described for the synthesis of (benzyloxycarbonyl-methoxy-methyl)-triphenyl-phosphonium chloride in example 114 a]) then gave 2(Z,E)-ethoxy-3-{3-fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-acrylic acid benzyl ester, which was hydrogenated to yield [rac]-2-ethoxy-3-{3-fluoro-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-propionic acid as colorless solid.
Sources & evidence
- ORD record
- ord-529962b04df649b7b6ed796bde29a822
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
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