Réaction #324426

ord-312fed1d8a574dd7bf5e643e5a198099

Équation de réaction

CO.Cl
HCl methanol
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O[C@@H]6OC[C@H](O)[C@H](O)[C@H]6O[C@@H]6O[C@@H](C)[C@H](O)[C@@H](O)[C@H]6O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]12
Pulchinenoside A
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]12
desired product
Rendement 85.0%
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CC[C@H](O)[C@@](C)(CO)[C@@H]5CC[C@]43C)[C@@H]12
3,23-Dihydroxy-20(29)-lupen-28-oic acid
Rendement 85.0%

Réactifs

Aucun

Solvants

Conditions de réaction

Température
35°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Extractionthe mixture was extracted with chloroform (3×50 ml)
  2. 2
    LavageThe combined organic layer was washed with H2O (1×10 ml), brine (1×10 ml)
  3. 3
    Séchagedried over sodium sulfate
  4. 4
    Concentrationconcentrated under vacuum
  5. 5
    AutreThe resulting residue was purified by column chromatography on silica gel

Mode opératoire

To a solution of HCl methanol reagent 10 (10 mL) was added Pulchinenoside A (DA001, 100 mg) and the resulting mixture was stirred at 35° C. for 4 days. After pouring into water (10 ml), the mixture was extracted with chloroform (3×50 ml). The combined organic layer was washed with H2O (1×10 ml), brine (1×10 ml), dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by column chromatography on silica gel using CH2Cl2-MeOH (v/v, 30:1) to yield the desired product as a white solid with 85% yield.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08642567B2uspto-grants-2014_02