Hydrochloric Acid → 4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(carboxymethylaminomethyl)indol-2-yl]isoindolinone

HRID 21019

Reaktionsgleichung

Reaktionsgleichung von HRID 21019
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:21][CH2:22][C:23]([O:25]CC)=[O:24])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35].[OH-].[Li+].Cl>CN(C=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:28]([O:30][C:31]([CH3:33])([CH3:32])[CH3:34])=[O:29])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:21][CH2:22][C:23]([OH:25])=[O:24])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:35]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 684889864-Chloro-7-[1-(tert-butoxycarbonyl)-5-(ethoxycarbonylmethylaminomethyl)indol-2-yl]isoindolinone

Produkt 1

HCID 684921274-Chloro-7-[1-(tert-butoxycarbonyl)-5-(carboxymethylaminomethyl)indol-2-yl]isoindolinoneAusbeute 61 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

4-Chloro-7-[1-(tert-butoxycarbonyl)-5-(ethoxycarbonylmethylaminomethyl)indol-2-yl]isoindolinone (43.4 mg) was dissolved in DMF (2 mL), and the solution was added with 4 mol/L aqueous lithium hydroxide solution (1 mL), followed by stirring at room temperature for 1 hour. The reaction mixture was added with 1 mol/L hydrochloric acid, extracted with ethyl acetate. The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure to obtain 4-chloro-7-[1-(tert-butoxycarbonyl)-5-(carboxymethylaminomethyl)indol-2-yl]isoindolinone (25.0 mg).

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-778c1b77740246e6a4b8de52e93d39dd
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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