DL-Carnitine → Acetyl carnitine chloride

HRID 1723086Notes

Reaction equation

HRID 1723086 reaction equation
C[O:2][CH2:3][C:4](O)=O.COCC([Cl:12])=O.[CH3:13][N+:14]([CH2:17][CH:18]([OH:23])[CH2:19][C:20]([O-:22])=[O:21])([CH3:16])[CH3:15]>C(#N)C>[C:3]([C:18]([CH2:19][C:20](=[O:22])[O-:21])([CH2:17][N+:14]([CH3:15])([CH3:16])[CH3:13])[OH:23])(=[O:2])[CH3:4].[Cl-:12]

Participants

5

Reactant 3

HCID 288DL-CarnitineHCID 12251Methoxyacetic AcidHCID 96623Methoxyacetyl chloride

Product 1

HCID 131713442Acetyl carnitine chlorideYield 83.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of methoxyacetic acid (3 ml; 0.04 moles) and methoxyacetyl chloride (3 ml; 0.03 moles) was kept under stirring at 30° C. for 2 hours. To this mixture carnitine chloride (4 g; 0.02 moles) which had been previously dried was added. The resulting mixture was brought to 40° C. and kept under stirring for seven days. The mixture was then taken up with acetonitrile and the unreacted carnitine chloride was filtered off. Upon addition of tert-butyl methyl ether an oil precipitated. The oil precipitation was repeated four times with acetonitrile/tert butyl methyl ether. The oil which finally separated was lyophilized. Four grams of mthoxy acetyl carnitine chloride were thus obtained.

Workup

  1. additionwas added
  2. customwas brought to 40° C.
  3. stirringunder stirring for seven days
  4. filtrationthe unreacted carnitine chloride was filtered off
  5. additionUpon addition of tert-butyl methyl ether an oil
  6. customprecipitated
  7. customThe oil precipitation
  8. customThe oil which finally separated

Sources & evidence

ORD record
ord-a69662da195c4cb28580ec39cf77c8de
Source dataset
uspto-grants-1989_08
Patent number
US04859698

Reaction notes

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