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Isobutylamine → (E)-N-isobutyl-diethylphosphonocrotonic acid amide

HRID 333042
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 333042
[CH2:1]([O:3][P:4]([CH2:9]/[CH:10]=[CH:11]/C(O)=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].Cl.C(N=C=NCCCN(C)C)C.[OH:27][C:28]1C2N=NNC=2C=CC=1.[CH2:37]([NH2:41])[CH:38]([CH3:40])[CH3:39].C(=O)([O-])[O-].[Na+].[Na+]>ClCCl>[CH2:37]([NH:41][C:28](=[O:27])/[C:9](/[P:4]([O:3][CH2:1][CH3:2])([O:6][CH2:7][CH3:8])=[O:5])=[CH:10]\[CH3:11])[CH:38]([CH3:40])[CH3:39]
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Komponenten

7

Edukt 5

HCID 6558IsobutylamineHCID 10340Sodium CarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 6285301(E)-4-(Diethoxyphosphoryl)but-2-enoic acidHCID 178418300HCID 178418300, Verbindung

Produkt 1

HCID 86698216
(E)-N-isobutyl-diethylphosphonocrotonic acid amide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A solution of 4-diethylphosphonocrotonic acid (5.0 g), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (5.2 g) and HO-Bt (hydroxybenzotriazole) (4.6 g) in dichloromethane (36.5 g) was stirred for 5 minutes under argon atmosphere. To the above reaction solution was added isobutylamine (4.9 mL), and the reaction solution was stirred at room temperature for 6 hours. A saturated sodium carbonate aqueous solution was added to the resulting reaction solution, and the water layer was extracted with dichloromethane. The combined organic layer was dried over anhydrous sodium sulfate. The organic solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetat→ethyl acetate/methanol=10/1) to give (E)-N-isobutyl-diethylphosphonocrotonic acid amide as colorless viscous oil.

Aufarbeitung

  1. extractionthe water layer was extracted with dichloromethane
  2. dry with materialThe combined organic layer was dried over anhydrous sodium sulfate
  3. concentrationThe organic solvent was concentrated under reduced pressure
  4. customthe residue was purified by silica gel chromatography (ethyl acetat→ethyl acetate/methanol=10/1)

Quellen und Nachweise

ORD-Eintrag
ord-35a3bd2771f648669ba905f318dc4934
Quelldatensatz
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08877953B2

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