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

HRID 2290386

Reaction equation

HRID 2290386 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. filtrationthe crystalline precipitate was filtered
  2. washwashed with ether
  3. customrecrystallized from ethyl acetate
  4. customto give 0.23 g

Sources & evidence

ORD record
ord-bf0c5188dc374255922da85e99c9b26b
Source dataset
uspto-grants-1986_10
Patent number
US04616038

Linked notes

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