Reaktion #63655

ord-f5d28144541a4d72ab9b187af1c7add8

Reaktionsgleichung

C[N+](C)(C)CC(O)CC(=O)[O-]
carnitine
CCOCC(=O)Cl
ethoxyacetyl chloride
CCOCC(=O)O
ethoxy acetic acid
CCOCC(=O)Cl
ethoxyacetyl chloride
C[N+](C)(C)CC(O)CC(=O)[O-]
carnitine chloride
CCOCC(=O)C(O)(CC(=O)[O-])C[N+](C)(C)C.[Cl-]
title compound
Ausbeute 75.0%
CCOCC(=O)C(O)(CC(=O)[O-])C[N+](C)(C)C.[Cl-]
ethoxy acetyl carnitine chloride
Ausbeute 75.0%

Reaktionsbedingungen

Temperatur
80°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Sonstigehad been prepared
  2. 2
    workup.ADDITIONwas added
  3. 3
    workup.WAITat 40° C. for eight days
  4. 4
    workup.WAITthe resulting mixture was kept at 40° C. for seven days
  5. 5
    workup.ADDITIONUpon addition
  6. 6
    Sonstigeprecipitated
  7. 7
    SonstigeThe oil precipitation
  8. 8
    Sonstigeuntil complete removal of the ethoxyacetic acid in excess

Vorschrift

A mixture of ethoxy acetic acid (5 ml; 0.07 moles) and ethoxyacetyl chloride (1.8 ml; 0.015 moles) which had been prepared as disclosed in step (b) of Example 5, was kept under stirring for 2 hours at 80° C. To this mixture carnitine chloride (2 g; 0.01 moles) which had been previously dried was added. The resulting mixture was first kept at 80° C. until complete dissolution of carnitine took place, then at 40° C. for eight days. A further amount of ethoxyacetyl chloride (0.9 ml; 0.007 moles) was added and the resulting mixture was kept at 40° C. for seven days. Upon addition to the mixture of tert-butyl methyl ether an oil precipitated. The oil precipitation was repeated four times with acetonitrile/tert butyl methyl ether until complete removal of the ethoxyacetic acid in excess. 1.5 grams of the title compound were thus obtained. Yield: 75%

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US04766222uspto-grants-1988_08