Potassium Iodide → (S)-3-{4-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester

HRID 1064894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1064894
[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[CH3:13].Cl[CH2:19][C:20]1[N:21]=[C:22]([C:26]2[CH:31]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=2)[O:23][C:24]=1[CH3:25].COC1C=C(C=C(OC)C=1)C=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]=[C:30]([O:32][CH3:33])[CH:29]=[C:28]([O:34][CH3:35])[CH:27]=3)[O:23][C:24]=2[CH3:25])=[CH:8][C:7]=1[CH3:13]

Komponenten

7

Edukt 6

HCID 4875Potassium IodideHCID 10796Cesium carbonateHCID 24813Phosphorus oxychlorideHCID 817473,5-DimethoxybenzaldehydeHCID 21974252Oxazole, 4-(chloromethyl)-2-(3,5-dimethoxyphenyl)-5-methyl-HCID 68616579(S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester

Produkt 1

HCID 69280726(S)-3-{4-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester

Versuchsvorschrift

In analogy to the procedure described in example 1 f], (2S)-2-ethoxy-3-(4-hydroxy-2-methyl-phenyl)-propionic acid methyl ester (example 1 d]) 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 2 a] and b]) in the presence of cesium carbonate and potassium iodide to yield (S)-3-{4-[2-(3,5-dimethoxy-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-methyl-phenyl}-2-ethoxy-propionic acid methyl ester as colorless liquid.

Aufarbeitung

  1. customexample 1 d

Quellen und Nachweise

ORD-Eintrag
ord-db21a1130dc54fd1ae0402df97e38b86
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969725B2

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