Réaction #556360

ord-f92f883b18c2454f9fa8077ecabde0e7

Équation de réaction

CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesterol
O=C(O)CBr
bromoacetic acid
→
CC(CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C)CC(=O)CBr
Bromoacetyl-Cholesterol
Rendement 73.0%

Réactifs

—
DIPC(N,N-diisopropylcarbodiimide)
CC(C)CCC[C@@H](C)[C@H]1CC[C@H]2[C@@H]3CC=C4C[C@@H](O)CC[C@]4(C)[C@H]3CC[C@]12C
cholesterol
O=C(O)CBr
bromoacetic acid

Réactifs

CN(C)c1ccncc1
DMAP

Solvants

ClCCl
dichloromethane
CCCCCC.CCOC(C)=O
n-hexane EtOAc

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    workup.WAITThe solution was left
  2. 2
    AutreThe solvent was evaporated
  3. 3
    Autrethe reaction product was purified by silica gel flash chromatography in n-hexane/dichloromethane 1/1
  4. 4
    workup.ADDITIONThe fractions containing the product
  5. 5
    Autreevaporated

Mode opératoire

A mixture of 100 mg of cholesterol and 40 mg of bromoacetic acid (1.1 eq) was dissolved in 10 mL of anhydrous dichloromethane. Then 44 μl (1.1 eq) of DIPC(N,N-diisopropylcarbodiimide) and 1.5 mg (0.05 eq) of DMAP (4-dimethylaminopyridine) were added. The solution was left stirring at room temperature for 48 h and analyzed by TLC using a mixture of n-hexane/EtOAc 10/1 as solvent systems. The solvent was evaporated and the reaction product was purified by silica gel flash chromatography in n-hexane/dichloromethane 1/1. The fractions containing the product were pooled, evaporated and then lyophilized in water/acetonitrile 20/80. The purified product was analyzed by NMR. Yield: 73%.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08629101B2uspto-grants-2014_01