Carboxy-N,N,N-trimethylmethanaminium → (-)-Carnitine

HRID 1612928

Reaction equation

HRID 1612928 reaction equation
C[N+](C[C@H](O)CC#N)(C)C.[Cl-].C[N+](CC(O)=O)(C)C.[CH3:20][N+:21]([CH2:24][CH:25]([OH:30])[CH2:26][C:27]([OH:29])=[O:28])([CH3:23])[CH3:22].[Cl-]>Cl>[OH:30][C@H:25]([CH2:26][C:27](=[O:28])[O-:29])[CH2:24][N+:21]([CH3:23])([CH3:20])[CH3:22]

Participants

5

Reactant 3

HCID 248Carboxy-N,N,N-trimethylmethanaminiumHCID 5970Carnitine ChlorideHCID 200829D(+)-CARNITINENITRILE CHLORIDE

Product 1

HCID 10917(-)-Carnitine

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

13.5 kg L-carnitine nitrile chloride was dissolved in 22 liters concentrated hydrochloric acid and hydrolyzed to L-carnitine chloride, as described in Example 2. It was subsequently reacted to betaine in the highly basic ion exchanger (Amberlite IRA-416). After appropriate reprocessing, 11.1 kg colorless L-carnitine with (α)D20 =-30.8° and an HPLC concentration of 99.7% was isolated.

Sources & evidence

ORD record
ord-62087cc445b44d86996435c802aaa79a
Source dataset
uspto-grants-1993_03
Patent number
US05191085

Linked notes

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