Trimethylamine → (-)-Carnitine

HRID 978325Notes

Reaction equation

C[O:2][C:3](=[O:9])[CH2:4][C@@H:5]([OH:8])[CH2:6]Cl.[CH3:10][N:11]([CH3:13])[CH3:12]>>[OH:8][C@H:5]([CH2:4][C:3](=[O:9])[O-:2])[CH2:6][N+:11]([CH3:13])([CH3:12])[CH3:10]

Participants

Reactant 2

HCID 1146Trimethylamine

HCID 10920707Methyl (R)-4-Chloro-3-hydroxybutyrate

Product 1

HCID 10917(-)-CarnitineYield 32%

Procedure

An amount of 100 g of (3R)-4-chloro-3-hydroxybutyrylamide of L-tyrosine methylester is submitted to methanolysis under the same operating conditions as reported in Example 2. An amount is obtained of 20 g (70%) of (3R)-4-chloro-3-hydroxybutyric acid methylester with [α]D20 =-23° (c=1.5 in CHCL3). (3R)-4-Chloro-3-hydroxybutyric acid methylester is treated with trimethylamine and L-carnitine is obtained (yield 32%).

Sources & evidence

ORD record: ord-baf89e5784a34c4194ea2a8d0eefe502
Source dataset: uspto-grants-1987_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04664852

Reaction notes

Loading…