Acetone → Cyclopentanpropionyl carnitine chloride

HRID 35374

Reaction equation

HRID 35374 reaction equation
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].[CH2:12]1[CH2:16][CH2:15][CH:14]([CH2:17][CH2:18][C:19]([Cl:21])=[O:20])[CH2:13]1.CC(C)=O>FC(F)(F)C(O)=O>[CH:14]1([CH2:17][CH2:18][C:19]([C:6]([CH2:7][C:8](=[O:10])[O-:9])([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[OH:11])=[O:20])[CH2:15][CH2:16][CH2:12][CH2:13]1.[Cl-:21]

Participants

5

Reactant 3

HCID 180AcetoneHCID 288DL-CarnitineHCID 660393-Cyclopentylpropionyl chloride

Product 1

HCID 131715700Cyclopentanpropionyl carnitine chlorideYield 90%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

Carnitine chloride (1.97 g; 0.01 moles) was dissolved in trifluoroacetic acid (10 cc). To the resulting solution 3-cyclopentanpropionyl chloride (1.60 g; 0.01 moles) was slowly added under stirring. The resulting mixture was kept under stirring at 45° C. overnight. The mixture was then cooled, acetone (40 ml) was added and the mixture was kept under stirring for 2 hours in ice. The precipitate thus formed was filtered off and to the filtrate ethyl ether was added. The white solid which precipitated was dissolved in ethanol-acetone (5:1) and once again precipitated with ether. M.P. 170°-172° C., yield 90%.

Workup

  1. stirringunder stirring at 45° C. overnight
  2. temperatureThe mixture was then cooled
  3. stirringunder stirring for 2 hours in ice
  4. customThe precipitate thus formed
  5. filtrationwas filtered off and to the filtrate ethyl ether
  6. additionwas added
  7. customThe white solid which precipitated
  8. dissolutionwas dissolved in ethanol-acetone (5:1)
  9. customonce again precipitated with ether

Sources & evidence

ORD record
ord-1c9e2b6c405c417fb12ccd9c82d0e996
Source dataset
uspto-grants-1988_08
Patent number
US04766222

Linked notes

Loading…