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

HRID 21018

Reaktionsgleichung

Reaktionsgleichung von HRID 21018
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH:20]=O)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29].Cl.[CH2:31]([O:33][C:34](=[O:37])[CH2:35][NH2:36])[CH3:32].C(N(CC)CC)C.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(#N)C.O>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][NH:36][CH2:35][C:34]([O:33][CH2:31][CH3:32])=[O:37])=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:29]

Komponenten

9

Edukt 6

HCID 176Acetic AcidHCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 2723640Glycine ethyl ester, hydrochlorideHCID 5049666Sodium triacetoxyborohydrideHCID 866282274-Chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone

Produkt 1

HCID 684889864-Chloro-7-[1-(tert-butoxycarbonyl)-5-(ethoxycarbonylmethylaminomethyl)indol-2-yl]isoindolinoneAusbeute 107,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

In a similar manner to Step 2 of Example 6, 4-chloro-7-[1-(tert-butoxycarbonyl)-5-formylindol-2-yl]isoindolinone (30.0 mg, 0.0730 mmol) was dissolved in acetonitrile (2 mL), and the solution was treated with glycine ethylester hydrochloride (41.0 mg, 0.294 mmol), triethylamine (0.081 mL, 0.58 mmol), acetic acid (0.084 mL, 1.5 mmol) and sodium triacetoxyborohydride (77.0 mg, 0.360 mmol). The reaction mixture was added with water and sodium hydrogen carbonate, followed by extracting 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-(ethoxycarbonylmethylaminomethyl)indol-2-yl]isoindolinone (39.2 mg).

Aufarbeitung

  1. extractionby extracting 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-10afc9e583d94f0e886213cb20eb6ff9
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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