Chloride → N-acetyl glutamyl carnitine hydrochloride

HRID 435479Notes

Reaction equation

HRID 435479 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(Cl)(Cl)[Cl:14].[Cl-].[C:18]([NH:21][C@H:22]([C:28](O)=[O:29])[CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:20])[CH3:19]>FC(F)(F)C(O)=O.C(OCC)C.CC(C)=O>[ClH:14].[C:18]([NH:21][C@H:22]([C:28]([C:3]([CH2:9][C:10](=[O:11])[O-:12])([CH2:4][N+:5]([CH3:8])([CH3:6])[CH3:7])[OH:2])=[O:29])[CH2:23][CH2:24][C:25](=[O:26])[OH:27])(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 312ChlorideHCID 6212ChloroformHCID 70914N-acetyl-L-glutamic acidHCID 97941973-Hydroxy-4-(trimethylammonio)butanoate hydrochloride

Product 1

HCID 131713077N-acetyl glutamyl carnitine hydrochloride

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 3283Diethyl EtherSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

4.2 g (0.021 moles) of carnitine hydrochloride are dissolved in 12 mls of trifluoroacetic acid, then at 35° C. and under vigorous stirring 20 cc of a solution of anhydrous chloroform wherein about 4.36 g (0.021 moles) of the acide chloride of the N-acetyl glutamic acid have been dissolved are added dropwise. The reaction is allowed to proceed for about 14 hours at 35° C., and subsequently at 50° C. for two further hours. The reaction mixture is cooled. Upon acetone addition (40 mls) no precipitate forms even though the mixture is cooled below 0° C. 140 mls of ethyl ether are added and after keeping the mixture at 8° C. overnight there are obtained 6.2 g of a solid white product which is crystallized with ethyl ether. After 2 crystallizations 5.4 g (68%) of the desired product having the following characteristics are obtained:

Workup

  1. dissolutionhave been dissolved
  2. additionare added dropwise
  3. customsubsequently at 50° C.
  4. temperatureThe reaction mixture is cooled
  5. temperatureis cooled below 0° C
  6. customat 8° C.
  7. customovernight

Sources & evidence

ORD record
ord-542c67c985bb42a79898f9ca484a9e7b
Source dataset
uspto-grants-1983_08
Patent number
US04401827

Reaction notes

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