Water → HCID 22320676, Verbindung

HRID 498083Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 498083
[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18](O)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[NH2:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=1.O.C(OCC)(=O)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:1]([N:5]([C:14]1[CH:22]=[CH:21][C:17]([C:18]([NH:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][N:25]=2)=[O:19])=[CH:16][CH:15]=1)[O:6][Si:7]([C:10]([CH3:12])([CH3:11])[CH3:13])([CH3:9])[CH3:8])([CH3:4])([CH3:2])[CH3:3]

Komponenten

7

Edukt 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 104392-AminopyridineHCID 113707224-[N-(tert-butyl)-N-(tert-butyldimethylsilyloxy)amino]-benzoic acid

Produkt 1

HCID 22320676HCID 22320676, VerbindungAusbeute 186,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of 1.0 g (3.09 mmol) of compound 2 in CH2Cl2 (5 mL) were added 0.733 g (3.71 mmol) of 1-(3-dimethylamino)propyl-3-ethylcarbodiimide hydrochloride, 0.189 g (1.545 mmol) of 4-dimethylaminopyridine, and 0.438 g (4.63 mmol) of 2-aminopyridine. After stirring for 12 hours at room temperature, H2O and ethyl acetate were added. The organic layer was separated, washed with sat'd NaHCO3 solution, dried over anhydrous MgSO4, filtered and concentrated under reduced pressure. The residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1) to give 2.3 g of compound 5 in 75% yield.

Aufarbeitung

  1. customThe organic layer was separated
  2. washwashed with sat'd NaHCO3 solution
  3. dry with materialdried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash column chromatography (silica, Hex:EtOAc=10:1)

Quellen und Nachweise

ORD-Eintrag
ord-b2a3804706a747d49165e5217ab6ade2
Quelldatensatz
uspto-grants-2005_09
Patentnummer
US06949654B2

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