반응 #502086

ord-ae05c6e12d1f40a1be49aa744b0431b9

반응 방정식

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2
→
C=C(C)[C@@H]1CC[C@]2(C(=O)O)CC[C@]3(C)[C@H](CC[C@@H]4[C@@]5(C)CCC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulonic acid

반응물

C=C(C)[C@@H]1CC[C@]2(C=O)CC[C@]3(C)[C@@H](CC[C@@H]4[C@@]5(C)C=CC(=O)C(C)(C)[C@@H]5CC[C@]43C)[C@@H]12
betulone aldehyde
OO
H2O2
[Na+].[O-][Cl+][O-]
NaClO2

시약

없음

용매

O
water
—
NaH2PO4.H2O
CC#N.O
CH3CN—H2O

반응 조건

온도
2.5°CELSIUS
상세 조건
See reaction.notes.procedure_details.

후처리

  1. 1
    온도the mixture warmed to room temperature
  2. 2
    기타The reaction is quenched by addition of Na2S2O5 (380 mg)
  3. 3
    추출extracted with ethyl acetate
  4. 4
    추출The organic extract
  5. 5
    세척is washed with water and brine
  6. 6
    건조dried (Na2SO4)
  7. 7
    여과filtered
  8. 8
    농축concentrated

실험 절차

The betulone aldehyde prepared from the last step is dissolved in a mixture of NaH2PO4.H2O (877 mg) and CH3CN—H2O (17 mL) and the suspension cooled to 0-5° C. 30% aqueous H2O2 (220 μL) and a solution of NaClO2 (200 mg) in water (16 mL) are then successively added, the mixture warmed to room temperature and stirred at this temperature for 1 h. The reaction is quenched by addition of Na2S2O5 (380 mg), and extracted with ethyl acetate. The organic extract is washed with water and brine, dried (Na2SO4), filtered, and concentrated. The residue is then subjected to column chromatography to afford betulonic acid (550 mg) as white solid.

출처

DOI: 10.6084/m9.figshare.5104873.v1특허: US08088757B2uspto-grants-2012_01