Nitrogen → Z-2-(2,2-Dimethylcyclopropanecarboxamido)-2-pentenoic acid

HRID 979428

Reaktionsgleichung

Reaktionsgleichung von HRID 979428
O=[C:2]([CH2:6][CH2:7][CH3:8])[C:3]([OH:5])=[O:4].[CH3:9][C:10]1([CH3:16])[CH2:12][CH:11]1[C:13]([NH2:15])=[O:14].O.N#N>C1(C)C=CC=CC=1>[CH3:9][C:10]1([CH3:16])[CH2:12][CH:11]1[C:13]([NH:15]/[C:2](=[CH:6]\[CH2:7][CH3:8])/[C:3]([OH:5])=[O:4])=[O:14]

Komponenten

6

Edukt 4

HCID 947NitrogenHCID 962WaterHCID 745632-Oxovaleric acidHCID 5747172,2-Dimethylcyclopropanecarboxamide

Produkt 1

HCID 13505564Z-2-(2,2-Dimethylcyclopropanecarboxamido)-2-pentenoic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

A solution of 1.74 g (15 mmole) of 2-ketovaleric acid and 1.13 g (10 mmole) of 2,2-dimethylcyclopropanecarboxamide in 20 ml of toluene was refluxed with stirring with collection of H2O in a small Dean-Stark trap. After 20 hrs. the solution was cooled and treated with a gentle stream of N2. Before much of the solvent had evaporated, crystallization was induced by scratching. After standing, the solid was collected on a filter and washed with toluene and some Et2O. Yield of white crystals=0.63 g (30%), mp 154.5°-155.5° (slight prelim. softening). Tlc (4:1 toluene-AcOH) showed only an extremely faint trace of the other isomer. NMR was consistent with the Z-configuration.

Aufarbeitung

  1. temperaturethe solution was cooled
  2. customBefore much of the solvent had evaporated
  3. customcrystallization
  4. customthe solid was collected on
  5. filtrationa filter
  6. washwashed with toluene

Quellen und Nachweise

ORD-Eintrag
ord-8427b7a31f544cc1bd6d48b44945daab
Quelldatensatz
uspto-grants-1987_05
Patentnummer
US04668504

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