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Isoamyl Nitrite → HCID 66614229, Verbindung

HRID 510128
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 510128
N[C:2]1[N:10]=[C:9]([C:11]2[C:19]3[C:14](=[N:15][CH:16]=[CH:17][CH:18]=3)[N:13]([CH2:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[F:27])[N:12]=2)[N:8]=[C:7]2[C:3]=1[N:4]([CH:29]1[CH2:32][CH2:31][CH2:30]1)[C:5](=[O:28])[NH:6]2.N(OCCC(C)C)=O.C(=O)([O-])O.[Na+]>O1CCCC1.[Cu](Cl)Cl>[CH:29]1([N:4]2[C:3]3[C:7](=[N:8][C:9]([C:11]4[C:19]5[C:14](=[N:15][CH:16]=[CH:17][CH:18]=5)[N:13]([CH2:20][C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=5[F:27])[N:12]=4)=[N:10][CH:2]=3)[NH:6][C:5]2=[O:28])[CH2:32][CH2:31][CH2:30]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8053Isoamyl NitriteHCID 516892Sodium BicarbonateHCID 66614413HCID 66614413, Verbindung

Produkt 1

HCID 66614229HCID 66614229, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24014Cupric ChlorideKatalysatorHCID 8028
Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

50 mg (0.12 mmol) of the compound from example 121 were initially charged in tetrahydrofuran (5 ml), then 0.11 ml (0.81 mmol) of isoamyl nitrite and 3 mg (0.02 mmol) of copper(II) chloride were added, and the mixture was stirred at RT overnight. The reaction mixture was admixed with saturated aqueous sodium hydrogencarbonate solution and extracted twice with ethyl acetate. The collected organic phases were dried over sodium sulfate, filtered and concentrated. The residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient). This gave 7 mg (13% of theory) of the title compound in solid form.

Aufarbeitung

  1. extractionextracted twice with ethyl acetate
  2. dry with materialThe collected organic phases were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by means of preparative HPLC (eluent: acetonitrile/water with 0.1% formic acid gradient)

Quellen und Nachweise

ORD-Eintrag
ord-7457b7e8e342406a9c448a056209ddae
Quelldatensatz
uspto-grants-2015_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09096592B2

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