N-bromobutanimide → HCID 86651794, Verbindung

HRID 2359809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2359809
[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([CH3:15])[N:10]=1)([CH3:4])([CH3:3])[CH3:2].C1C(=O)N([Br:31])C(=O)C1>C(#N)C>[C:1]([O:5][C:6](=[O:23])[CH2:7][N:8]([C:9]1[CH:14]=[CH:13][C:12]([Br:31])=[C:11]([CH3:15])[N:10]=1)[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])([CH3:3])([CH3:4])[CH3:2]

Komponenten

4

Edukt 2

HCID 67184N-bromobutanimideHCID 86651793N-[(1,1-Dimethylethoxy)carbonyl]-N-(6-methyl-2-pyridinyl)glycine 1,1-dimethylethyl ester

Produkt 1

HCID 86651794HCID 86651794, VerbindungAusbeute 95,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

To a solution of tert-butyl[tert-butoxycarbonyl(6-methylpyridin-2-yl)amino]-acetate (477 mg, 1.48 mmol) obtained in Reference Example 1-(a) in acetonitrile (3 ml) was added NBS (398 mg, 2.24 mmol), followed by stirring at 40° C. for 3 hours. After completion of the reaction, the reaction solution was concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; hexane:ethyl acetate=20:1→5:1 (V/V)), and fractions containing the desired compound were concentrated under reduced pressure to afford the title compound (565 mg) as a white solid. (Yield: 95%)

Aufarbeitung

  1. customAfter completion of the reaction
  2. concentrationthe reaction solution was concentrated under reduced pressure
  3. additioncontaining the desired compound
  4. concentrationwere concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-b021a5b40e364769a7ab1c99f617ef90
Quelldatensatz
uspto-grants-2014_04
Patentnummer
US08685986B2

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