Sodium Methoxide → 8-(4-Fluoro-phenoxy)-4-hydroxy-isoquinoline-3-carboxylic acid methyl ester
Reaktionsgleichung
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)[C:6]=1[CH2:19][N:20]([CH2:31][C:32]([O:34][CH3:35])=[O:33])S(C1C=CC(C)=CC=1)(=O)=O)C.C[O-].[Na+]>CO>[CH3:35][O:34][C:32]([C:31]1[N:20]=[CH:19][C:6]2[C:5]([C:4]=1[OH:3])=[CH:10][CH:9]=[CH:8][C:7]=2[O:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:33]Komponenten
4
Edukt 2
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
To a stirred solution of 3-(4-fluoro-phenoxy)-2-{[methoxycarbonylmethyl-(toluene-4-sulfonyl)-amino]-methyl}-benzoic acid ethyl ester (2.66 g, 5.17 mmol) in anhydrous methanol (8 mL) was added dropwise a solution of sodium methoxide (30% wt, 2.8 mL) and methanol (2 mL) at 0° C. The mixture was stirred at 0° C. for 10 minutes and then 3 h at room temperature before it was concentrated in vacuo. Water was added and the pH of the slurry was adjusted with 1 N HCl to pH=10. The resulting precipitate was collected by filtration, washed with water, saturated sodium bicarbonate, and water, and was dried in vacuo to give the title compound as a white solid (1.51 g): MS: (+) m/z 314.07 (M+1).
Aufarbeitung
- customat 0° C
- concentration3 h at room temperature before it was concentrated in vacuo
- additionWater was added
- filtrationThe resulting precipitate was collected by filtration
- washwashed with water, saturated sodium bicarbonate, and water
- customwas dried in vacuo
Quellen und Nachweise
- ORD-Eintrag
- ord-1f9fff5cf9a94d52bf18801a19914c2b
- Quelldatensatz
- uspto-grants-2015_11
- Patentnummer
- US09174976B2
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