Potassium Iodide → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-benzofuran-7-yl}-2-ethoxy-propionic acid methyl ester

HRID 479201Notes

Reaction equation

HRID 479201 reaction equation
[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[O:13][CH:12]=[CH:11][C:10]=2[C:9]([OH:15])=[CH:8][CH:7]=1.[C:20]([C:24]1[CH:29]=[CH:28][C:27]([C:30]2[O:31][C:32]([CH3:37])=[C:33]([CH2:35]Cl)[N:34]=2)=[CH:26][CH:25]=1)([CH3:23])([CH3:22])[CH3:21].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:19])[CH:4]([O:16][CH2:17][CH3:18])[CH2:5][C:6]1[C:14]2[O:13][CH:12]=[CH:11][C:10]=2[C:9]([O:15][CH2:35][C:33]2[N:34]=[C:30]([C:27]3[CH:26]=[CH:25][C:24]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:29][CH:28]=3)[O:31][C:32]=2[CH3:37])=[CH:8][CH:7]=1

Participants

5

Reactant 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 121582182-(4-Tert-butyl-phenyl)-4-chloromethyl-5-methyl-oxazoleHCID 686172122-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester

Product 1

HCID 69557215[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-benzofuran-7-yl}-2-ethoxy-propionic acid methyl ester

Procedure

In analogy to the procedure described in example 120 f], 2-ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester (example 120 e]) was reacted with 2-(4-tert-butyl-phenyl)-4-chloromethyl-5-methyl-oxazole in the presence of potassium carbonate and potassium iodide to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-benzofuran-7-yl}-2-ethoxy-propionic acid methyl ester, which was further saponified in analogy to the procedure described in example 120 f] to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-benzofuran-7-yl}-2-ethoxy-propionic acid as white solid.

Sources & evidence

ORD record
ord-6206191dabee4742912d76ebd022b361
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

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