Oleanolic Acid → (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

HRID 2190248Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2190248
[CH3:1][C@@:2]12[C@H:11]3[CH2:12][CH:13]=[C:14]4[C@@H:19]5[CH2:20][C:21]([CH3:25])([CH3:24])[CH2:22][CH2:23][C@:18]5([C:26]([OH:28])=[O:27])[CH2:17][CH2:16][C@@:15]4([CH3:29])[C@:10]3([CH3:30])[CH2:9][CH2:8][C@H:7]1[C:6]([CH3:32])([CH3:31])[C@@H:5]([OH:33])[CH2:4][CH2:3]2.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>C(Cl)Cl>[CH3:24][C:21]1([CH3:25])[CH2:22][CH2:23][C@@:18]2([C:26]([OH:28])=[O:27])[CH:19]([C:14]3[C@@:15]([CH3:29])([CH2:16][CH2:17]2)[C@@:10]2([CH3:30])[CH:11]([C@:2]4([CH3:1])[CH:7]([CH2:8][CH2:9]2)[C:6]([CH3:32])([CH3:31])[C:5](=[O:33])[CH2:4][CH2:3]4)[CH2:12][CH:13]=3)[CH2:20]1

Komponenten

4

Edukt 2

HCID 10494Oleanolic AcidHCID 159087Triacetoxyperiodinane

Produkt 1

HCID 470665(4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-3,4,5,6,6a,7,8,8a,11,12,13,14b-dodecahydro-1H-picene-4a-carboxylic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a mixture of oleanolic acid (Ia, 5.0 g, 10.9 mmol) and CH2Cl2 (200 mL) was added the Dess-Martin reagent (6.0 g, 14.2 mmol) under nitrogen at room temperature. After stirring at room temperature for 1 hour, the starting material was consumed, as indicated by TLC (1:1 hexanes:diethyl ether). The reaction mixture was quenched with the addition of a solution of sodium thiosulfate and NaHCO3 (50 g sodium thiosulfate in 200 mL saturated NaHCO3 solution). The mixture was stirred at room temperature for 10 minutes. The layers were separated and the aqueous layer was extracted with EtOAc (3×250 mL).

Aufarbeitung

  1. customthe starting material was consumed
  2. customThe reaction mixture was quenched with the addition of a solution of sodium thiosulfate and NaHCO3 (50 g sodium thiosulfate in 200 mL saturated NaHCO3 solution)
  3. stirringThe mixture was stirred at room temperature for 10 minutes
  4. customThe layers were separated
  5. extractionthe aqueous layer was extracted with EtOAc (3×250 mL)

Quellen und Nachweise

ORD-Eintrag
ord-1cf6790b4ec04edcb7105f16fe96256f
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08324264B1

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