Potassium Carbonate → [Rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-isopropoxy-phenyl}-2-ethoxy-propionic acid ethyl ester

HRID 1065019Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1065019
[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[CH:9][C:8]=1[O:14][CH:15]([CH3:17])[CH3:16])[CH3:2].[C:22]([C:26]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][C:34]([CH3:39])=[C:35]([CH2:37]Cl)[N:36]=2)=[CH:28][CH:27]=1)([CH3:25])([CH3:24])[CH3:23].C(C1C=CC(C=O)=CC=1)(C)(C)C.O=P(Cl)(Cl)Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:21])[CH:5]([O:18][CH2:19][CH3:20])[CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:37][C:35]2[N:36]=[C:32]([C:29]3[CH:28]=[CH:27][C:26]([C:22]([CH3:25])([CH3:24])[CH3:23])=[CH:31][CH:30]=3)[O:33][C:34]=2[CH3:39])=[CH:9][C:8]=1[O:14][CH:15]([CH3:16])[CH3:17])[CH3:2]

Komponenten

7

Edukt 5

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 703244-tert-ButylbenzaldehydeHCID 121582182-(4-Tert-butyl-phenyl)-4-chloromethyl-5-methyl-oxazoleHCID 69280498[Rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester

Produkt 1

HCID 69283426[Rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-isopropoxy-phenyl}-2-ethoxy-propionic acid ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In analogy to the procedure described in example 1 f], [rac]-2-ethoxy-3-(4-hydroxy-2-isopropoxy-phenyl)-propionic acid ethyl ester was reacted with 2-(4-tert-butyl-phenyl)-4-chloromethyl-5-methyl-oxazole (prepared from 4-tert-butyl-benzaldehyde and diacetyl monoxyme followed by treatment with POCl3 in analogy to the procedures described in examples 5 a] and 2 b]) in N,N-dimethylformamide in the presence of potassium carbonate to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-isopropoxy-phenyl}-2-ethoxy-propionic acid ethyl ester, which was further saponified in analogy to the procedure described in example 1 g], to yield [rac]-3-{4-[2-(4-tert-butyl-phenyl)-5-methyl-oxazol-4-ylmethoxy]-2-isopropoxy-phenyl}-2-ethoxy-propionic acid as colorless viscous oil, which can be separated into its antipodes by methods known in the art, such as separation of the antipodes via diastereomeric salts by crystallization with optically pure amines such as e.g. (R) or (S)-1-phenyl-ethylamine, (R) or (S)-1-naphthalen-1-yl-ethylamine, brucine, quinine and quinidine or by separation of the antipodes by specific chromatographic methods using either a chiral adsorbens or a chiral eluent to give the title compound.

Quellen und Nachweise

ORD-Eintrag
ord-08bb7930942f40ca95e6b50c23aca2a6
Quelldatensatz
uspto-grants-2005_11
Patentnummer
US06969725B2

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