Trimethylamine → (-)-Carnitine

HRID 1920279Notes

Reaction equation

HRID 1920279 reaction equation
[OH-].[Na+].[CH3:3][N:4]([CH3:6])[CH3:5].Cl[CH2:8][C@H:9]([OH:16])[CH2:10][C:11]([O:13]CC)=[O:12]>O>[OH:16][C@H:9]([CH2:10][C:11](=[O:12])[O-:13])[CH2:8][N+:4]([CH3:6])([CH3:5])[CH3:3]

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 14798Sodium HydroxideHCID 27344454-Chloro-3-hydroxybutyric acid ethyl ester, (3R)-

Product 1

HCID 10917(-)-Carnitine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

Water (1777 g), aqueous sodium hydroxide (50%, 203.7 g, 1.5 eq.) and aqueous trimethylamine (25%, 807 g, 2.0 eq.) were mixed and stirred at 0° C. Ethyl (R)-4-chloro-3-hydroxybutyrate (content 91.7%, 307.9 g) was added dropwise during 3 h and the procedure was continued as described in Example 1.

Sources & evidence

ORD record
ord-8340f31a4ccf40d4935e6bc4a67b3d58
Source dataset
uspto-grants-2012_05
Patent number
US08168823B2

Reaction notes

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