DL-Carnitine → Tert-butyl acetyl carnitine chloride

HRID 35371

Reaction equation

HRID 35371 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:12](CC([Cl:19])=O)([CH3:15])([CH3:14])[CH3:13].[CH3:20][CH2:21][O:22]CC>FC(F)(F)C(O)=O>[C:12]([CH:5]([N+:2]([CH3:3])([CH3:4])[CH3:1])[C:6]([C:21](=[O:22])[CH3:20])([CH2:7][C:8](=[O:10])[O-:9])[OH:11])([CH3:15])([CH3:14])[CH3:13].[Cl-:19]

Participants

5

Reactant 3

HCID 288DL-CarnitineHCID 3283Diethyl EtherHCID 815143,3-Dimethylbutanoyl chloride

Product 1

HCID 131715696Tert-butyl acetyl carnitine chlorideYield 80%

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 solution tert-butyl acetyl chloride (1.4 cc; 0.01 moles) was slowly added under stirring. The resulting mixture was kept under stirring at room temperature for 48 hours. To the mixture Et2O was added and the thus obtained precipitate was filtered off. The raw product was crystallized from isopropanol-ethyl ether, thus obtaining a pure product. MP 164°-165° C. Yield 80%

Workup

  1. stirringunder stirring at room temperature for 48 hours
  2. filtrationthe thus obtained precipitate was filtered off
  3. customThe raw product was crystallized from isopropanol-ethyl ether
  4. customthus obtaining a pure product

Sources & evidence

ORD record
ord-02fba49a08984876a7c07be75ff83bf6
Source dataset
uspto-grants-1988_08
Patent number
US04766222

Linked notes

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