tert-Butyl carbazate → tert-butyl N'-[2-(2-chloroethoxy)-2-(6-chloropyridin-3-yl)acetyl]hydrazinecarboxylate

HRID 599643Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 599643
C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C.[Cl:20][CH2:21][CH2:22][O:23][CH:24]([C:28]1[CH:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:25]([OH:27])=O.[C:35]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])(=[O:38])[NH:36][NH2:37]>CN(C=O)C.O.C(OCC)(=O)C.C(Cl)CCl>[Cl:20][CH2:21][CH2:22][O:23][CH:24]([C:28]1[CH:29]=[N:30][C:31]([Cl:34])=[CH:32][CH:33]=1)[C:25]([NH:37][NH:36][C:35]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])=[O:27]

Komponenten

9

Edukt 4

HCID 70091tert-Butyl carbazateHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 86615151(2-Chloroethoxy)-(6-chloropyridin-3-yl)acetic acid

Produkt 1

HCID 86615150tert-butyl N'-[2-(2-chloroethoxy)-2-(6-chloropyridin-3-yl)acetyl]hydrazinecarboxylateAusbeute 72,6 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 111,2-DichloroethaneLösungsmittelHCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

HOBT (681 mg), IPEA (1.98 mL) and EDC (966 mg) were sequentially added to a solution of (2-chloroethoxy)-(6-chloropyridin-3-yl)acetic acid (630 mg) and tert-butyl carbazate (400 mg) in DMF (15 mL), and the reaction solution was stirred at room temperature for three hours. Ethyl acetate and water were added to the reaction solution, and the organic layer was separated. The resulting organic layer was washed with brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent solvent: heptane:ethyl acetate=1:2) to obtain 666 mg of the title compound. The property value of the compound is as follows.

Aufarbeitung

  1. customthe organic layer was separated
  2. washThe resulting organic layer was washed with brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluent solvent: heptane:ethyl acetate=1:2)

Quellen und Nachweise

ORD-Eintrag
ord-6ac33b98ed464f58b189f30641fbdba2
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07897632B2

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