2-Oxobutanoic Acid → HCID 13505570, compound

HRID 2290387Notes

Reaction equation

HRID 2290387 reaction equation
O=[C:2]([CH2:6][CH3:7])[C:3]([OH:5])=[O:4].[CH2:8]([C:10]1([CH2:16][CH3:17])[CH2:12][CH:11]1[C:13]([NH2:15])=[O:14])[CH3:9]>C1(C)C=CC=CC=1>[CH2:8]([C:10]1([CH2:16][CH3:17])[CH2:12][CH:11]1[C:13]([NH:15]/[C:2](=[CH:6]\[CH3:7])/[C:3]([OH:5])=[O:4])=[O:14])[CH3:9]

Participants

4

Reactant 2

HCID 582-Oxobutanoic AcidHCID 2409772,2-Diethylcyclopropane-1-carboxamide

Product 1

HCID 13505570HCID 13505570, compoundYield 9.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2.3 g of 2-ketobutyric acid, 2.0 g of 2,2-diethylcyclopropanecaboxamide, and 25 ml of toluene was heated under reflux for 16 hrs with removal of H20 by a modified Dean-Stark trap containing molecular sieves (4A). No product precipitated upon cooling. Ether (25 ml) was added and the mixture was extracted with saturated NaHCO3 (3 times). The combined extracts were acidified with concentrated HCl. The gummy precipitate crystallized when triturated with water. Recrystallization from ethyl acetate gave 0.31 g of product, m.p. 129°-30°. The NMR spectrum was consistent with the desired structure.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 16 hrs with removal of H20 by a modified Dean-Stark trap
  3. customNo product precipitated
  4. temperatureupon cooling
  5. additionEther (25 ml) was added
  6. extractionthe mixture was extracted with saturated NaHCO3 (3 times)
  7. customThe gummy precipitate crystallized when
  8. customtriturated with water
  9. customRecrystallization from ethyl acetate

Sources & evidence

ORD record
ord-3485c41d5e294e2783efca9b8a6f1e82
Source dataset
uspto-grants-1986_10
Patent number
US04616038

Reaction notes

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