(Benzyloxycarbonyl-ethoxy-methyl)-triphenyl-phosphonium chloride → [Rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3-propyl-phenyl}-propionic acid
Reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[CH:10][C:11]=1[O:12][CH2:13][CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[O:18][C:19]=1[CH3:20])C=O)[CH:2]=[CH2:3].[Cl-].C([O:35][C:36]([CH:38]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:39][CH2:40][CH3:41])=[O:37])C1C=CC=CC=1.[Cl-].[CH2:62](OC(C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)OC)=O)C1C=CC=CC=1>>[CH2:40]([O:39][CH:38]([CH2:62][C:6]1[CH:9]=[CH:10][C:11]([O:12][CH2:13][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=3)[O:18][C:19]=2[CH3:20])=[C:4]([CH2:1][CH2:2][CH3:3])[CH:5]=1)[C:36]([OH:35])=[O:37])[CH3:41]Participants
Reactant 3
Product 1
Procedure
In analogy to the procedures described in examples 114 b], c] and d], 3-allyl-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-allyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-benzaldehyde. Treatment of 3-allyl-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 3-{3-allyl-4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-phenyl}-2(Z,E)-ethoxy-acrylic acid benzyl ester, which was hydrogenated to yield [rac]-2-ethoxy-3-{4-[2-(5-methyl-2-phenyl-oxazol-4-yl)-ethoxy]-3-propyl-phenyl}-propionic acid as colorless solid.
Sources & evidence
- ORD record
- ord-0fd367147df44592a335b73939480185
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
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