Potassium Iodide → HCID 69283472, compound

HRID 1065009Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:18])[C@@H:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[CH3:14])C.Cl[CH2:20][C:21]1[N:22]=[C:23]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[O:24][CH:25]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:3][C:4](=[O:18])[C@@H:5]([O:15][CH2:16][CH3:17])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:20][C:21]2[N:22]=[C:23]([C:26]3[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=3)[O:24][CH:25]=2)=[CH:9][C:8]=1[CH3:14]

Participants

Reactant 4

HCID 4875Potassium Iodide

HCID 10796Cesium carbonate

HCID 35511964-(Chloromethyl)-2-phenyl-1,3-oxazole

HCID 69283330HCID 69283330, compound

Product 1

HCID 69283472HCID 69283472, compound

Procedure

In analogy to the procedure described in example 1 f], (S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid ethyl ester (example 1 d]) was reacted with 4-chloromethyl-2-phenyl-oxazole [prepared from benzamide and 1,3-dichloroacetone as described in Bioorg. Med. Chem. Lett. (2000), 10(17), 2041-2044] in the presence of cesium carbonate and potassium iodide to yield (S)-2-ethoxy-3-[2-methyl-4-(2-phenyl-oxazol-4-ylmethoxy)-phenyl]-propionic acid methyl ester as colorless liquid.

Workup

customexample 1 d

Sources & evidence

ORD record: ord-9a31ca0af176465182154ea9dad941dc
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

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