Potassium Iodide → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2,3-dihydro-benzofuran-7-yl}-2-ethoxy-propionic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[C:10]([OH:16])=[CH:9][CH:8]=1)[CH3:2].[C:21]([C:25]1[CH:30]=[CH:29][C:28]([C:31]2[O:32][C:33]([CH3:38])=[C:34]([CH2:36]Cl)[N:35]=2)=[CH:27][CH:26]=1)([CH3:24])([CH3:23])[CH3:22].C(=O)([O-])[O-].[K+].[K+].[I-].[K+]>>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([O:17][CH2:18][CH3:19])[CH2:6][C:7]1[C:15]2[O:14][CH2:13][CH2:12][C:11]=2[C:10]([O:16][CH2:36][C:34]2[N:35]=[C:31]([C:28]3[CH:27]=[CH:26][C:25]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:30][CH:29]=3)[O:32][C:33]=2[CH3:38])=[CH:9][CH:8]=1)[CH3:2]Participants
5
Reactant 4
Product 1
Procedure
In analogy to the procedure described in example 120 f], [rac]-2-ethoxy-3-(4-hydroxy-2,3-dihydro-benzofuran-7-yl)-propionic acid ethyl ester (example 125 a]) was reacted with 2-(4-tert-butyl-phenyl)-4-chloromethyl-5-methyl-oxazole (example 123 a]) in the presence of potassium carbonate and potassium iodide to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2,3-dihydro-benzofuran-7-yl}-2-ethoxy-propionic acid ethyl 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]-2,3-dihydro-benzofuran-7-yl}-2-ethoxy-propionic acid as white solid.
Sources & evidence
- ORD record
- ord-1db9f6d1dd0d402b8dd7bfd0e18a866f
- Source dataset
- uspto-grants-2003_11
- Patent number
- US06642389B2
Reaction notes
Loading…