ChemicalBook CAS DataBase List 3-Oxo-olean-12-en-28-oic acid

3-Oxo-olean-12-en-28-oic acid synthesis

4synthesis methods

Product Name:3-Oxo-olean-12-en-28-oic acid
CAS Number:17990-42-0
Molecular formula:C30H46O3
Molecular Weight:454.68

508-02-1 Synthesis

508-02-1
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17990-42-0
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Yield:17990-42-0 99%

Reaction Conditions:

with Dess-Martin periodane in dichloromethane at 20; for 1 h;Inert atmosphere;

Steps:

III.i (i) Preparation of Ib: (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
(i)
Preparation of Ib: (4aS,6aS,6bR,12aR)-2,2,6a,6b,9,9,12a-Heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylic acid
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 mmo l) 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 x 250 mL).
The combined organics were dried (Na₂SO₄), filtered and concentrated under reduced pressure.
The residue was purified by column chromatography (silica, 3:1 hexanes/diethyl ether) to provide the sub-title compound (4.9 g, 99%) as a white foam.
¹H NMR (300 MHz, CDCl₃) 0.81 (s, 3H), 0.90-2.05 (m, 39H), 2.42-2.44 (m, 1H), 2.59-2.61 (m, 1H), 2.83-2.85 (m, 1H), 5.29-5.31 (m, 1H). ESI MS m/z 455 [C₃₀H₄₆O₃ + H]⁺.

References:

Sequoia Sciences, Inc.;Eldridge, Gary R.;Buckle, Ronald Neil;Ellis, Michael;Huang, Zhongping;Reilly, John Edward EP2712863, 2014, A1 Location in patent:Paragraph 0040

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