4-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane → 3-((2S,3S)-3-amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile

HRID 2354503

Reaktionsgleichung

Reaktionsgleichung von HRID 2354503
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[CH:10]([N:12]=[N+]=[N-])[CH3:11])=[CH:4][CH:3]=1>C(OC(C)C)(=O)C.[Pd].CC([O-])=O.CC([O-])=O.[Pb+2]>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C@@H:9]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]#[N:22])[CH:16]=2)[C@@H:10]([NH2:12])[CH3:11])=[CH:4][CH:3]=1

Komponenten

4

Edukt 1

HCID 116811424-(4-Chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane

Produkt 1

HCID 115872963-((2S,3S)-3-amino-1-(4-chlorophenyl)butan-2-yl)benzonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 131709914Lindlars catalystKatalysatorHCID 7915Isopropyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
21.5 °C

Versuchsvorschrift

To a solution of 4-(4-chlorophenyl)-3-(3-cyanophenyl)-2-azidobutane (650 g, 2.1 mol) in isopropyl acetate (3.3 L) was added Lindlar's catalyst (130 g), and the mixture was hydrogenated at 40 psi at 45° C. for 24 h and at room temperature for anther 48 h. The reaction mixture was filtered over solka floc, and the cake was washed thoroughly with isopropyl acetate. The filtrate was partially concentrated to approximately 6 L, and was added hydrogen chloride in isopropyl acetate (5-6 N) while maintaining the reaction temperature at 18-25° C. After aging overnight, the precipitate was collected by filtration and washed twice with isopropyl acetate (1 L×2). The precipitate was suspended in isopropyl acetate (5.8 L) and was added aqueous potassium carbonate (1 M, 3.5 L). After stirring for 20 min, the organic layer was separated and concentrated to an oil, which was purified by preparative HPLC eluting on a Chiralpak AD column with heptane/ethanol/diethylamine (70/30/0.1; flow rate: 700 mL/min) to give the title compound.

Aufarbeitung

  1. filtrationThe reaction mixture was filtered over solka floc
  2. washthe cake was washed thoroughly with isopropyl acetate
  3. concentrationThe filtrate was partially concentrated to approximately 6 L
  4. additionwas added hydrogen chloride in isopropyl acetate (5-6 N)
  5. waitAfter aging overnight
  6. filtrationthe precipitate was collected by filtration
  7. washwashed twice with isopropyl acetate (1 L×2)
  8. additionwas added aqueous potassium carbonate (1 M, 3.5 L)
  9. customthe organic layer was separated
  10. concentrationconcentrated to an oil, which
  11. customwas purified by preparative HPLC
  12. washeluting on a Chiralpak AD column with heptane/ethanol/diethylamine (70/30/0.1; flow rate: 700 mL/min)

Quellen und Nachweise

ORD-Eintrag
ord-f74c6c3e2e154a0c9708b8ad429ef3a3
Quelldatensatz
uspto-grants-2010_07
Patentnummer
US07754188B2

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