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Methanol → HCID 12344670, Verbindung

HRID 327794
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 327794
[NH2:1][C@H:2]([C:6]([OH:8])=O)[CH:3]([CH3:5])[CH3:4].[C:9](OC(=O)C)(=[O:11])[CH3:10].N1C=CC=C[CH:17]=1.CO>CN(C)C1C=CN=CC=1.C(OCC)C>[C:9]([NH:1][CH:2]([CH:3]([CH3:5])[CH3:4])[C:6](=[O:8])[CH3:17])(=[O:11])[CH3:10]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 887MethanolHCID 1049PyridineHCID 6287L-ValineHCID 7918Acetic Anhydride

Produkt 1

HCID 12344670HCID 12344670, VerbindungAusbeute 19,1 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridine
Katalysator
HCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A mixture of L-valine (25.0 g, 0.21 mol), acetic anhydride (60.5 ml, 0.64 mol), pyridine (52 ml, 0.64 mol) and 4-dimethylaminopyridine (2.0 g, 16.6 mmol) was heated at reflux overnight. The reaction mixture was allowed to cool to room temperature and methanol added with rapid stirring. The mixture was concentrated under reduced pressure to give an oil which was dissolved in diethyl ether (250 ml), washed with 2M hydrochloric acid (150 ml), saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml) dried over anhydrous magnesium sulphate, filtered and evaporated. Distillation under reduced pressure gave N-acetyl-2-keto-3-amino-4-methylpentane (6.3 g, 19%) as a viscous straw coloured oil (76°-78° C. @ 1.5 mm Hg).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux overnight
  3. concentrationThe mixture was concentrated under reduced pressure
  4. customto give an oil which
  5. washwashed with 2M hydrochloric acid (150 ml), saturated aqueous sodium hydrogen carbonate (150 ml) and brine (150 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. distillationDistillation under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-daa57e43b4a04c3ba1de67505d5040a9
Quelldatensatz
uspto-grants-1993_12
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05274094

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