DL-Carnitine → Tert-butyl acetyl carnitine chloride

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

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%