Réaction #2487410

ord-9c12b277724249c9bb672d83b6bca669

Équation de réaction

O=C(O)CCCC[C@@H]1CCSS1
lipoic acid
O=C1CCC(=O)N1O
N-hydroxysuccinimide
ClCCCl
EDC
NC(=O)CCCC[C@@H]1CCSS1
(R)-Lipoamide

Réactifs

Aucun

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Lavagewashed with H2O (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NaCl (500 mL)
  2. 2
    Séchagedried (MgSO4)
  3. 3
    AutreThe drying agent was removed by filtration
  4. 4
    Concentrationthe filtrate was concentrated to dryness
  5. 5
    Autregiving the product as

Mode opératoire

A solution of lipoic acid (25.6 g, 124 mmol), N-hydroxysuccinimide (15.6 g, 136 mmol), and EDC (26.1 g, 136 mmol) in anhydrous CH2Cl2 (300 mL) was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate (500 mL) and washed with H2O (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NaCl (500 mL) and dried (MgSO4). The drying agent was removed by filtration and the filtrate was concentrated to dryness giving the product as a yellow sold (35.4 g, 94%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08795706B2uspto-grants-2014_08