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 2190248노트

반응식

HRID 2190248 반응식
[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

참가 물질

4

반응물 2

HCID 10494Oleanolic AcidHCID 159087Triacetoxyperiodinane

생성물 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

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-1cf6790b4ec04edcb7105f16fe96256f
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08324264B1

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