Ethanol → 1,3-Diethyl 2-[[[2-(4-amino-1H-indol-1-yl)acetyl]oxy]methyl]-2-phenylpropanedioate

HRID 494407Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 494407
[CH2:1]([O:3][C:4](=[O:34])[C:5]([CH2:17][O:18][C:19](=[O:33])[CH2:20][N:21]1[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]([N+]([O-])=O)=[CH:22]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH3:2].C(O)C.O.[Cl-].[NH4+:40]>O1CCCC1>[CH2:9]([O:8][C:6](=[O:7])[C:5]([CH2:17][O:18][C:19](=[O:33])[CH2:20][N:21]1[C:29]2[C:24](=[C:25]([NH2:40])[CH:26]=[CH:27][CH:28]=2)[CH:23]=[CH:22]1)([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:34])[CH3:10]

Komponenten

6

Edukt 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 68765445HCID 68765445, Verbindung

Produkt 1

HCID 576832531,3-Diethyl 2-[[[2-(4-amino-1H-indol-1-yl)acetyl]oxy]methyl]-2-phenylpropanedioateAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

The 2-[2-(3-Nitroindol-1-yl)acetoxymethyl]-2-phenylmalonic acid diethyl ester (100 mg) obtained in Example 9c) was dissolved in tetrahydrofuran (2 mL), ethanol (4 mL) and water (1 mL), and to the solution were added ammonium chloride (57 mg) and reduced iron (60 mg). The mixture was stirred at 100° C. for 2 hours, cooled, and filtered through a Celite pad. The filtrate was concentrated and diluted with ethyl acetate. The extract was washed successively with saturated aqueous sodium bicarbonate, water and saturated brine, dried over sodium sulfate, and concentrated to give the title compound (93 mg).

Aufarbeitung

  1. temperaturecooled
  2. filtrationfiltered through a Celite pad
  3. concentrationThe filtrate was concentrated
  4. additiondiluted with ethyl acetate
  5. washThe extract was washed successively with saturated aqueous sodium bicarbonate, water and saturated brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-4de822049c474fd78ebc45544b7820ef
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07538140B2

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