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
Reaction equation
[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]1Participants
4
Procedure
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).
Workup
- customthe starting material was consumed
- 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)
- stirringThe mixture was stirred at room temperature for 10 minutes
- customThe layers were separated
- extractionthe aqueous layer was extracted with EtOAc (3×250 mL)
Sources & evidence
- ORD record
- ord-1cf6790b4ec04edcb7105f16fe96256f
- Source dataset
- uspto-grants-2012_12
- Patent number
- US08324264B1
Reaction notes
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