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 2190248ノート

反応式

HRID 2190248 の反応式
[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

参加物

4

反応物 2

HCID 10494Oleanolic AcidHCID 159087Triacetoxyperiodinane

生成物 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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-1cf6790b4ec04edcb7105f16fe96256f
出典データセット
uspto-grants-2012_12
特許番号
US08324264B1

反応ノート

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