Potassium Iodide → HCID 69557067, compound

HRID 479219Notes

Reaction equation

HRID 479219 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.Cl[CH2:21][C:22]1[N:23]=[C:24]([C:28]2[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=2)[O:25][C:26]=1[CH3:27].COC1C=C(C=C(OC)C=1)C=O.O=P(Cl)(Cl)Cl.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][CH2:21][C:22]2[N:23]=[C:24]([C:28]3[CH:33]=[C:32]([O:34][CH3:35])[CH:31]=[C:30]([O:36][CH3:37])[CH:29]=3)[O:25][C:26]=2[CH3:27])=[CH:8][CH:7]=1

Participants

7

Reactant 6

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 817473,5-DimethoxybenzaldehydeHCID 21974252Oxazole, 4-(chloromethyl)-2-(3,5-dimethoxyphenyl)-5-methyl-HCID 686172122-Ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester

Product 1

HCID 69557067HCID 69557067, compound

Procedure

In analogy to the procedure described in example 120 f], [rac]-2-ethoxy-3-(4-hydroxy-benzofuran-7-yl)-propionic acid methyl ester (example 120 e]) was reacted with 4-chloromethyl-2-(3,5-dimethoxy-phenyl)-5-methyl-oxazole (prepared from 3,5-dimethoxy-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 21 a] and b]) in the presence of potassium carbonate and potassium iodide to yield [rac]-3-{4-[2-(3,5-dimethoxy-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-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethoxy]-benzofuran-7-yl}-2-ethoxy-propionic acid as colorless solid.

Sources & evidence

ORD record
ord-ca867b5da2034cb8b6979e174b7f6017
Source dataset
uspto-grants-2003_11
Patent number
US06642389B2

Reaction notes

Loading…