Potassium Iodide → HCID 69280476, compound

HRID 1064932Notes

Reaction equation

[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][C:7]=1[F:13].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[F:32])[O:23][C:24]=1[CH3:25].FC1C=CC=CC=1C=O.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[K+]>>[CH3:1][O:2][C:3](=[O:17])[C@@H:4]([O:14][CH2:15][CH3:16])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:19][C:20]2[N:21]=[C:22]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=3[F:32])[O:23][C:24]=2[CH3:25])=[CH:8][C:7]=1[F:13]

Participants

Reactant 6

HCID 4875Potassium Iodide

HCID 10796Cesium carbonate

HCID 24813Phosphorus oxychloride

HCID 67970o-Fluorobenzaldehyde

HCID 44411144-Chloromethyl-2-(2-fluoro-phenyl)-5-methyl-oxazole

HCID 68617914HCID 68617914, compound

Product 1

HCID 69280476HCID 69280476, compound

Procedure

In analogy to the procedure described in example 1 f], (2S)-2-ethoxy-3-(2-fluoro-4-hydroxy-phenyl)-propionic acid methyl ester (example 13 f]) was reacted with 4-chloromethyl-2-(2-fluoro-phenyl)-5-methyl-oxazole (prepared from 2-fluoro-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 5 a] and 2 b]) in the presence of cesium carbonate and potassium iodide to yield (S)-2-ethoxy-3-{2-fluoro-4-[2-(2-fluoro-phenyl)-5-methyl-oxazol-4-ylmethoxy]-phenyl}-propionic acid methyl ester as colorless liquid.

Sources & evidence

ORD record: ord-fa86b16ff18a46e3bcb6761c2a4a94e4
Source dataset: uspto-grants-2005_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06969725B2

Reaction notes

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