DL-Carnitine → Tert-butyl acetyl carnitine chloride

HRID 1723082Notes

Reaction equation

HRID 1723082 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 chloride

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 te 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.

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-6c0b231226ef41f08c5a0483636f6389
Source dataset
uspto-grants-1989_08
Patent number
US04859698

Reaction notes

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