Reacción #2487410

ord-9c12b277724249c9bb672d83b6bca669

Ecuación de reacción

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

Reactivos

Ninguno

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Lavadowashed with H2O (500 mL), saturated aqueous NaHCO3 (500 mL), saturated aqueous NaCl (500 mL)
  2. 2
    Secadodried (MgSO4)
  3. 3
    OtroThe drying agent was removed by filtration
  4. 4
    Concentraciónthe filtrate was concentrated to dryness
  5. 5
    Otrogiving the product as

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US08795706B2uspto-grants-2014_08