2-Oxoadipic acid → Z-2-(2,2-Dimethylcyclopropanecarboxamido)-2-hexenedioic acid

HRID 1885843Notes

Reaction equation

HRID 1885843 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:4][CH:3]1[C:5]([NH2:7])=[O:6].O=[C:10]([CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])[C:11]([OH:13])=[O:12].C(OC)(=O)CC(C)C>O>[CH3:1][C:2]1([CH3:8])[CH2:4][CH:3]1[C:5]([NH:7]/[C:10](=[CH:14]\[CH2:15][CH2:16][C:17]([OH:19])=[O:18])/[C:11]([OH:13])=[O:12])=[O:6]

Participants

5

Reactant 3

HCID 712-Oxoadipic acidHCID 11160Methyl isovalerateHCID 5747172,2-Dimethylcyclopropanecarboxamide

Product 1

HCID 13505568Z-2-(2,2-Dimethylcyclopropanecarboxamido)-2-hexenedioic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.0 g. of 2,2-dimethylcyclopropanecarboxamide, 2.4 g. of 2-ketoadipic acid and 25 ml. of methyl isovalerate was heated under reflux for 4 hrs, with removal of H2O by a modified Dean-Stark trap containing molecular sieves (4A). After standing at room temperature overnight, the crystalline precipitate was filtered, washed with ether and recrystallized from ethyl acetate to give 0.23 g. of product, m.p. 163°-165°. The NMR spectrum was consistent with the desired structure.

Workup

  1. additionA mixture of 1.0 g
  2. filtrationthe crystalline precipitate was filtered
  3. washwashed with ether
  4. customrecrystallized from ethyl acetate
  5. customto give 0.23 g

Sources & evidence

ORD record
ord-6c9efdd49c5246b9b0b6d3dc80fbdb72
Source dataset
uspto-grants-1992_09
Patent number
US05147868

Reaction notes

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