Pyridine → HCID 69804279, Verbindung

HRID 488646Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 488646
[CH3:1][O:2][C:3]([NH:5][CH:6]([CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=1)[C:7]([OH:9])=[O:8])=[O:4].N1C=CC=CC=1.[CH3:30][Si:31]([CH3:36])([CH3:35])[CH2:32][CH2:33]O.C1(N=C=NC2CCCCC2)CCCCC1>C(#N)C>[CH3:30][Si:31]([CH3:36])([CH3:35])[CH2:32][CH2:33][O:8][C:7](=[O:9])[CH:6]([NH:5][C:3]([O:2][CH3:1])=[O:4])[CH2:10][C:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:14]([N+:21]([O-:23])=[O:22])=[CH:13][CH:12]=1

Komponenten

6

Edukt 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 180132-(Trimethylsilyl)ethanolHCID 22271898HCID 22271898, Verbindung

Produkt 1

HCID 69804279HCID 69804279, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6342AcetonitrileLösungsmittel

Versuchsvorschrift

To a mixture of 2-methoxycarbonylamino-3-(4-nitro-naphthalen-1-yl)-propionic acid (0.35 g, 1.1 mmol), pyridine (0.78 mL) and 2-trimethylsilylethanol (0.18 mL, 1.25 mmol, 1.1 eq) in acetonitrile (1.1 mL) cooled in an ice bath was added dicyclohexylcarbodiimide (0.25 g, 1.21 mmol). The mixture was stirred cold for 1 hour, placed in the refrigerator for 14 hours. The reaction mixture was filtered, concentrated under reduced pressure and purified on silica gel eluting with heptane/ethyl acetate (4:1) to provide the titled compound. MS ESI(−)) m/e 417 (M−H)−.

Aufarbeitung

  1. temperaturecooled in an ice bath
  2. waitplaced in the refrigerator for 14 hours
  3. filtrationThe reaction mixture was filtered
  4. concentrationconcentrated under reduced pressure
  5. custompurified on silica gel eluting with heptane/ethyl acetate (4:1)

Quellen und Nachweise

ORD-Eintrag
ord-83c81e26247840328c7f2013da31a54b
Quelldatensatz
uspto-grants-2005_12
Patentnummer
US06972340B2

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