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

HRID 979428

반응식

HRID 979428 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-8427b7a31f544cc1bd6d48b44945daab
출처 데이터셋
uspto-grants-1987_05
특허 번호
US04668504

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