Hydrochloric Acid → 4-[Benzyl-(4-methoxy-benzenesulfonyl)-amino]-7-trifluoromethylquinoline-3-carboxylic acid

HRID 1861634

Reaktionsgleichung

C([O:3][C:4]([C:6]1[CH:7]=[N:8][C:9]2[C:14]([C:15]=1[N:16]([CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])=[CH:13][CH:12]=[C:11]([C:35]([F:38])([F:37])[F:36])[CH:10]=2)=[O:5])C.[OH-].[Na+].Cl>CO.C1COCC1>[CH2:28]([N:16]([S:17]([C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)(=[O:19])=[O:18])[C:15]1[C:14]2[C:9](=[CH:10][C:11]([C:35]([F:37])([F:38])[F:36])=[CH:12][CH:13]=2)[N:8]=[CH:7][C:6]=1[C:4]([OH:5])=[O:3])[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Komponenten

Reaktionsbedingungen

Temperatur: 25 °C

Versuchsvorschrift

To a solution of 1.065 g (2.00 mmol) of the product from Example 1 in 4 mL of methanol/THF (1:1) was added 2 mL of 1N sodium hydroxide solution and the resulting mixture was stirred at 25° C. for 18 h. The reaction was then acidified with 1N HCl and extracted with ethyl acetate (200 mL). The organic layer was washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was triturated with ethyl acetate/hexane (1:9) and filtered to provide 828 mg (82%) of the desired carboxylic acid as a white solid. Electrospray Mass Spec 517.1 (M+H)

Aufarbeitung

extractionextracted with ethyl acetate (200 mL)
washThe organic layer was washed with water and brine
dry with materialdried over MgSO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe resulting residue was triturated with ethyl acetate/hexane (1:9)
filtrationfiltered

Quellen und Nachweise

ORD-Eintrag: ord-8169476c951f407994a91d7b34f8247f
Quelldatensatz: uspto-grants-2003_03
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US06534491B2

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