Water → {4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid

HRID 1715856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1715856
C[O:2][C:3](=[O:36])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:35])[NH:12][C:13]2[CH:22]=[C:21]3[C:16]([CH2:17][CH2:18][CH2:19][N:20]3[S:23]([C:26]3[CH:31]=[C:30]([Cl:32])[CH:29]=[CH:28][C:27]=3[O:33][CH3:34])(=[O:25])=[O:24])=[CH:15][CH:14]=2)=[CH:7][CH:6]=1.[Li+].[OH-].O>CO.O1CCCC1>[Cl:32][C:30]1[CH:29]=[CH:28][C:27]([O:33][CH3:34])=[C:26]([S:23]([N:20]2[C:21]3[C:16](=[CH:15][CH:14]=[C:13]([NH:12][C:11]([C:8]4[CH:9]=[CH:10][C:5]([CH2:4][C:3]([OH:36])=[O:2])=[CH:6][CH:7]=4)=[O:35])[CH:22]=3)[CH2:17][CH2:18][CH2:19]2)(=[O:25])=[O:24])[CH:31]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 3939Lithium HydroxideHCID 68434762{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester

Produkt 1

HCID 24961622{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21899815MeOH tetrahydrofuranLösungsmittel

Versuchsvorschrift

{4-[1-(5-Chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid methyl ester (121.00 mg, 0.23 mmol) was dissolved in methanol/tetrahydrofuran 1:1 (1.40 mL) and treated at room temperature with a 1N solution of LiOH in water (0.70 mL, 0.70 mmol). The mixture was stirred at room temperature for 4 hours, then the organic solvents were evaporated and the residual aqueous phase acidified with HCl 1N (0.70 mL). The precipitated solid was filtered washing with ether, then purified by flash chromatography (dichloromethane/methanol gradient) to yield {4-[1-(5-chloro-2-methoxy-benzenesulfonyl)-1,2,3,4-tetrahydro-quinolin-7-ylcarbamoyl]-phenyl}-acetic acid as an off-white solid, 69.00 mg (59%), MS (ISP): m/e=513.5 (M−H).

Aufarbeitung

  1. customthe organic solvents were evaporated
  2. filtrationThe precipitated solid was filtered
  3. washwashing with ether
  4. custompurified by flash chromatography (dichloromethane/methanol gradient)

Quellen und Nachweise

ORD-Eintrag
ord-0dbaf10588a94acd83031bd1250615dc
Quelldatensatz
uspto-grants-2010_09
Patentnummer
US07799933B2

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