Lithium Hydroxide → {5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid

HRID 890422Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 890422
C([O:3][C:4](=[O:37])[CH2:5][N:6]1[C:14]2[C:9](=[CH:10][C:11]([O:15][CH2:16][C:17]3[C:18]([CH2:33][CH2:34][O:35][CH3:36])=[N:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=4)=[N:21][CH:22]=3)=[CH:12][CH:13]=2)[CH:8]=[CH:7]1)C.[OH-].[Li+]>C1COCC1>[CH3:36][O:35][CH2:34][CH2:33][C:18]1[C:17]([CH2:16][O:15][C:11]2[CH:10]=[C:9]3[C:14](=[CH:13][CH:12]=2)[N:6]([CH2:5][C:4]([OH:37])=[O:3])[CH:7]=[CH:8]3)=[CH:22][N:21]=[C:20]([C:23]2[CH:24]=[CH:25][C:26]([C:29]([F:32])([F:30])[F:31])=[CH:27][CH:28]=2)[N:19]=1

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 69641981{5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester

Produkt 1

HCID 11248727{5-[4-(2-Methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acidAusbeute 83,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

A solution of 147 mg (0.29 mmol) {5-[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid ethyl ester and 0.9 ml 1N lithium hydroxide solution in 1.5 ml THF were stirred over night at RT. The reaction mixture was partitioned between ether, 1N HCl and water. The residue was suspended in ether/heptane 1:9 and the resulting crystals were filtered off to give 118 mg of pure {5-[4-(2-methoxy-ethyl)-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-indol-1-yl}-acetic acid.

Aufarbeitung

  1. customThe reaction mixture was partitioned between ether, 1N HCl and water
  2. filtrationthe resulting crystals were filtered off

Quellen und Nachweise

ORD-Eintrag
ord-ef39872262c04ab39c24eb4b6e9b641b
Quelldatensatz
uspto-grants-2006_02
Patentnummer
US06995263B2

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