Water → HCID 69241992, Verbindung

HRID 1394131Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1394131
[C:1]([O:5][C:6]([N:8]1[CH2:12][C@H:11](OS(C)(=O)=O)[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].O.[CH3:26][N:27](C=O)C>[C-]#N.C([N+](CCCC)(CCCC)CCCC)CCC>[C:1]([O:5][C:6]([N:8]1[CH2:12][C@@H:11]([C:26]#[N:27])[CH2:10][C@H:9]1[C:18]([N:20]1[CH2:24][CH2:23][S:22][CH2:21]1)=[O:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Komponenten

5

Edukt 3

HCID 962WaterHCID 6228DimethylformamideHCID 87425656HCID 87425656, Verbindung

Produkt 1

HCID 69241992HCID 69241992, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 165872Tetrabutylammonium CyanideKatalysator

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

To a solution of Example 17B (16.55 g, 44 mmol) in dry DMF (100 mL) under nitrogen was added tetrabutylammonium cyanide (50 g, 200 mmol). The mixture was heated to 50° C. for 60 hours and then poured into cold water and extracted with ethyl acetate (3×250 mL). The combined organic layers were dried (magnesium sulfate) and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane to provide the titled compound (12 g). MS (ESI) m/e 312 (M+H)+, 310 (M−H)−; 1H NMR (400 MHz, CD3OD) δ ppm 1.44 (m, 9H) 2.10 (m, 1H) 2.79 (m, 1H) 3.05 (m, 1H) 3.17 (m, 1H) 3.33 (m, 1H) 3.57 (dd, 1H) 3.83 (m, 2H) 3.96 (m, 1H) 4.48 (m, 1H) 4.65 (m, 2H).

Aufarbeitung

  1. extractionextracted with ethyl acetate (3×250 mL)
  2. dry with materialThe combined organic layers were dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by flash silica gel chromatography with 50% ethyl acetate/50% hexane

Quellen und Nachweise

ORD-Eintrag
ord-d386c51c6fa74d5ba0d4b64ee60d39e1
Quelldatensatz
uspto-grants-2008_03
Patentnummer
US07348346B2

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