Butyric Acid → HCID 59537267, compound

HRID 2090592Notes

Reaction equation

HRID 2090592 reaction equation
[C:1]([OH:6])(=O)[CH2:2][CH2:3][CH3:4].[NH2:7][C:8]1[CH2:13][CH2:12][CH2:11][C:10](=[O:14])[CH:9]=1.CN(C1C=CC=CN=1)C.C(N(C(C)C)CC)(C)C.C(N=C=NCCCN(C)C)C>ClCCl>[O:14]=[C:10]1[CH2:11][CH2:12][CH2:13][C:8]([NH:7][C:1](=[O:6])[CH2:2][CH2:3][CH3:4])=[CH:9]1

Participants

7

Reactant 5

HCID 264Butyric AcidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 218852-DimethylaminopyridineHCID 788923-Aminocyclohex-2-en-1-oneHCID 81531Diisopropylethylamine

Product 1

HCID 59537267HCID 59537267, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Butyric acid (465 mg, 5.28 mmol) and 3-amino-2-cyclohexene-1-one (645 mg, 5.81 mmol) were dissolved in dichloromethane (50 mL). Dimethylaminopyridine (750 mg, 5.81 mmol), diisopropylethylamine (774 mg, 6.34 mmol) and 1-ethyl-3-dimethylaminopropyl carbodiimide (1.13 g, 5.81 mmol) were added to the resulting mixture, followed by stirring at room temperature for about 14 hours. The reaction mixture was concentrated under reduced pressure. The resulting residue was purified using silica gel chromatography (developing solvent: n-hexane/ethyl acetate=6/4) to obtain the N-(3-oxo-cyclohexen-1-yl)butyramide (1a-1) shown by the formula below.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customThe resulting residue was purified

Sources & evidence

ORD record
ord-30df88ce69834cfba702534c1202f0a7
Source dataset
uspto-grants-2013_05
Patent number
US08436210B2

Reaction notes

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