tert-Butyl methyl ether → 4-Methoxybutyryl carnitine

HRID 280583Notes

Reaction equation

HRID 280583 reaction equation
Cl.[OH:2][CH:3]([CH2:9][C:10](=[O:12])[O-:11])[CH2:4][N+:5]([CH3:8])([CH3:7])[CH3:6].[CH3:13][O:14][CH2:15][CH2:16][CH2:17][C:18](Cl)=[O:19].COC(C)(C)C>FC(F)(F)C(O)=O>[CH3:13][O:14][CH2:15][CH2:16][CH2:17][C:18]([C:3]([CH2:9][C:10](=[O:11])[O-:12])([CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7])[OH:2])=[O:19]

Participants

5

Reactant 3

HCID 15413tert-Butyl methyl etherHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochlorideHCID 127949894-Methoxybutanoyl chloride

Product 1

HCID 1317146834-Methoxybutyryl carnitineYield 50%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4.5 g (0.02 moles) of carnitine hydrochloride were dissolved in 6 ml of trifluoroacetic acid. To this solution 4-methoxybutyryl chloride was added. The resulting mixture was kept under stirring at room temperature for 16 days. Subsequently tert-butyl methyl ether was added to the mixture. An oil precipitated which was treated with anhydrous acetonitrile in order to remove the undesired carnitine. To the acetonitrile solution tert-butyl methyl ether was added and 4-methoxybutyryl carnitine precipitated. Yield 50%.

Workup

  1. customAn oil precipitated which
  2. additionwas treated with anhydrous acetonitrile in order
  3. customto remove the undesired carnitine
  4. additionTo the acetonitrile solution tert-butyl methyl ether was added
  5. custom4-methoxybutyryl carnitine precipitated

Sources & evidence

ORD record
ord-010f40dc76444bb5a34c1c8b116783bb
Source dataset
uspto-grants-1986_05
Patent number
US04590209

Reaction notes

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