DL-Carnitine → 4-Carbomethoxy butyryl carnitine chloride

HRID 35375

Reaction equation

HRID 35375 reaction equation
[CH3:1][N+:2]([CH2:5][CH:6]([OH:11])[CH2:7][C:8]([O-:10])=[O:9])([CH3:4])[CH3:3].C(OCC)C.[C:17]([CH2:21][CH2:22][CH2:23][C:24]([Cl:26])=[O:25])([O:19][CH3:20])=[O:18]>C(O)(C(F)(F)F)=O>[C:17]([CH2:21][CH2:22][CH2:23][C:24]([C:6]([CH2:7][C:8](=[O:10])[O-:9])([CH2:5][N+:2]([CH3:3])([CH3:4])[CH3:1])[OH:11])=[O:25])([O:19][CH3:20])=[O:18].[Cl-:26]

Participants

5

Reactant 3

HCID 288DL-CarnitineHCID 3283Diethyl EtherHCID 73916Methyl 4-chloroformylbutyrate

Product 1

HCID 1317157024-Carbomethoxy butyryl carnitine chloride

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of carnitine chloride (2.0 g; 10 m moles) in TFA (5 cc), 4-carbomethoxy butyryl chloride (1.65 cc; 12 m moles) was added and the resulting reaction mixture was kept at room temperature under stirring for 24 hours. To this mixture anhydrous ethyl ether was then added. A solid formed which was filtered off and crystallized from hot isopropanol. M.P. 130°-132° C.

Workup

  1. customthe resulting reaction mixture
  2. customwas kept at room temperature
  3. customA solid formed which
  4. filtrationwas filtered off
  5. customcrystallized from hot isopropanol

Sources & evidence

ORD record
ord-96f8a0ff3c6b4f4ea6fcbcff987e883e
Source dataset
uspto-grants-1988_08
Patent number
US04766222

Linked notes

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