Diethyl Ether → Pivaloyl carnitine hydrochloride

HRID 435474Notes

Reaction equation

HRID 435474 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:13]([Cl:19])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15].CCOCC>C(O)(C(F)(F)F)=O.CC(C)=O>[ClH:19].[C:13]([C:3]([CH2:9][C:10](=[O:11])[O-:12])([CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7])[OH:2])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 3

HCID 3283Diethyl EtherHCID 62493Pivaloyl chlorideHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochloride

Product 1

HCID 131713068Pivaloyl carnitine hydrochlorideYield 60%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

1.98 g (0.01 moles) of carnitine hydrochloride are dissolved in 3 mls of CF3COOH, and to the solution an excess (7 mls) of pivalic acid chloride is added. The solution is kept under stirring at room temperature for about 48 hours. At the end of this period of time, the mixture is diluted with 20 mls of acetone and some ether is slowly added till complete precipitation. The mixture is filtered and the precipitate which has the tendency to become hygroscopic is quickly washed with ether and dried under vacuum at the temperature of about 50° C. 1.70 g are obtained with a yield of 60% of a product having the following characteristics:

Workup

  1. filtrationThe mixture is filtered
  2. washis quickly washed with ether
  3. customdried under vacuum at the temperature of about 50° C

Sources & evidence

ORD record
ord-2dceb28f405b4873b307888aa8ee56ff
Source dataset
uspto-grants-1983_08
Patent number
US04401827

Reaction notes

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