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

HRID 979428

反応式

HRID 979428 の反応式
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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8427b7a31f544cc1bd6d48b44945daab
出典データセット
uspto-grants-1987_05
特許番号
US04668504

関連ノート

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