Acetone → Allyl acetyl-carnitine

HRID 463040Notes

Reaction equation

HRID 463040 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].C([CH2:16][C:17](Cl)=[O:18])C=C.[CH3:20][C:21]([CH3:23])=O>FC(F)(F)C(O)=O>[CH2:23]([CH:4]([N+:5]([CH3:8])([CH3:6])[CH3:7])[C:3]([C:17](=[O:18])[CH3:16])([CH2:9][C:10](=[O:11])[O-:12])[OH:2])[CH:21]=[CH2:20]

Participants

5

Reactant 3

HCID 180AcetoneHCID 42284934-Pentenoyl chlorideHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochloride

Product 1

HCID 131714223Allyl acetyl-carnitineYield 66%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of carnitine hydrochloride (9 grams; 0.045 moles) in 15 cc of trifluoroacetic acid, 0.13 moles of allyl acetyl chloride were added. The resulting solution was kept at 45° C. for 4 hours. Subsequently, acetone was added to the solution, the unreacted carnitine was separated and ethyl ether was added, thus obtaining a precipitate. The raw material thus obtained was purified by precipitation from isopropanol--ethyl ether. 9.5 grams of product were obtained. Yield 66%.

Workup

  1. customthe unreacted carnitine was separated
  2. additionethyl ether was added
  3. customthus obtaining a precipitate
  4. customThe raw material thus obtained
  5. customwas purified by precipitation from isopropanol

Sources & evidence

ORD record
ord-cd258ba1a94c4719ad24c060aee284c1
Source dataset
uspto-grants-1985_05
Patent number
US04518613

Reaction notes

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