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

HRID 479198Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].[I-].[K+].[CH3:9][O:10][C:11](=[O:27])[CH:12]([O:24][CH2:25][CH3:26])[CH2:13][C:14]1[C:22]2[O:21][CH:20]=[CH:19][C:18]=2[C:17]([OH:23])=[CH:16][CH:15]=1.Cl[CH2:29][C:30]1[N:31]=[C:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[O:33][C:34]=1[CH3:35]>CN(C)C=O>[CH3:9][O:10][C:11](=[O:27])[CH:12]([O:24][CH2:25][CH3:26])[CH2:13][C:14]1[C:22]2[O:21][CH:20]=[CH:19][C:18]=2[C:17]([O:23][CH2:29][C:30]2[N:31]=[C:32]([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[O:33][C:34]=2[CH3:35])=[CH:16][CH:15]=1

Participants

Conditions

Temperature: 80 °C

Procedure

Potassium carbonate (37 mg, 300 μmol, 1.4 eq.) and potassium iodide (4 mg, 30 μmol, 0.1 eq.) were added to a solution of [rac]-2-ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester (50 mg, 189 μmol) and 4-chloromethyl-5-methyl-2-phenyl-oxazole (39 mg, 189 μmol, 1 eq.) in N,N-dimethylformamide (0.5 ml). The mixture was shaken at 80° C. for 12 h, filtered off and the filtrate evaporated in vacuo to give [rac]-2-ethoxy-3-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzofuran-7-yl]-propionic acid methyl ester. Crude [rac]-2-ethoxy-3-[4-(5-methyl-2-phenyl-oxazol-4-ylmethoxy)-benzofuran-7-yl]-propionic acid methyl ester was dissolved in a 2:1:1 mixture of THF/ethanol/water. Lithium hydroxide (40 mg, 945 μmol, 5 eq.) was added and the solution was shaken at ambient temperature for 12 h. Acidification with 25% aqueous hydrochloric acid and evaporation of the solvent in vacuo were followed by purification through a preparative HPLC column to give the title compound (28 mg, 66 μmol, 35%) as white solid.

Workup

filtrationfiltered off
customthe filtrate evaporated in vacuo

Sources & evidence

ORD record: ord-7fa67678764843c38aa0fdf97f45fac8
Source dataset: uspto-grants-2003_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06642389B2

Reaction notes

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