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218600-53-4

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Basic Information
CAS No.: 218600-53-4
Name: Bardoxolone methyl
Article Data: 11
Molecular Structure:
Molecular Structure of 218600-53-4 (Bardoxolone methyl)
Formula: C32H43 N O4
Molecular Weight: 505.698
Synonyms: 2-Cyano-3,12-dioxooleana-1,9(11)-dien-28-oicacid methyl ester; Bardoxolone methyl; CDDO Methylester; CDDO-Me; Methyl 2-cyano-3,12-dioxoleana-1,9(11)-dien-28-oate; NSC713200; RTA 402
Density: 1.15g/cm3
Melting Point: 215-223°C
Boiling Point: 600.8°Cat760mmHg
Flash Point: 256.5°C
PSA: 84.23000
LogP: 6.37898
Related products
Synthetic route
1428550-98-4

2-bromo-3,12-dioxo-oleanane-1,9 (11)-diene-28-carboxylic acid methyl ester

copper(l) cyanide

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 120℃; for 30h;83.6%
With potassium iodide In N,N-dimethyl-formamide at 120℃;73%
With potassium iodide In N,N-dimethyl-formamide at 120℃;73%
With potassium iodide In N,N-dimethyl-formamide at 120℃; for 24h; Temperature; Time; Reagent/catalyst; Inert atmosphere;66%
67-56-1

methanol

218600-44-3

bardoxolone

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
Stage #1: bardoxolone With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 20℃; for 1.16667h; Cooling with ice;
Stage #2: methanol In dichloromethane for 1h;		96%

methyl 2-cyano-3,12-dioxoolean-9(11)-en-28-oate

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.5h; Reflux; Inert atmosphere;87%
Stage #1: methyl 2-cyano-3,12-dioxoolean-9(11)-en-28-oate With Phenylselenyl chloride In ethyl acetate
Stage #2: With dihydrogen peroxide In tetrahydrofuran; water		40%
With Phenylselenyl chloride; dihydrogen peroxide 1.) ethyl acetate, 2.) THF; Yield given; Multistep reaction;
1198076-59-3

C31H43IO4

copper(l) cyanide

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
With potassium iodide In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere;89%
305818-40-0

1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.5h; Heating;92%

1-hydroxyl-2-cyano-3-(4-(methyl-L-glutaminate-N5-yl)-benzyloxy)-12-oxo-oleana-2(3),9(11)-dien-28-oic acid methyl ester

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
With porcine liver esterase; γ-glutamyl transpeptidase In aq. buffer at 37℃; for 8h; pH=7.4; Enzymatic reaction;88%
508-02-1

Oleanolic acid

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
3.2: 24 h / 35 °C / Inert atmosphere
4.1: potassium iodide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
3.2: 90 °C / Inert atmosphere; Darkness
3.3: 18 h / 37 °C / Inert atmosphere
4.1: potassium iodide / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 4 steps
1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 0 - 20 °C / Inert atmosphere
2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
3.2: 90 °C / Inert atmosphere; Darkness
4.1: potassium iodide / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
View Scheme
69660-90-8

(4aS,6aS,6bR,8aR,12aR,12bR,14bS)-methyl2,2,6a,6b,9,9,12a-heptamethyl-10-oxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,12b,13,14b-octadecahydropicene-4a-carboxylate

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
1.2: 24 h / 35 °C / Inert atmosphere
2.1: potassium iodide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
1.2: 90 °C / Inert atmosphere; Darkness
1.3: 18 h / 37 °C / Inert atmosphere
2.1: potassium iodide / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
2: hydrogen bromide; bromine; acetic acid
3: potassium iodide / N,N-dimethyl-formamide / 120 °C
View Scheme
Multi-step reaction with 3 steps
1: 3-chloro-benzenecarboperoxoic acid / dichloromethane
2: hydrogen bromide; bromine; acetic acid
3: potassium iodide / N,N-dimethyl-formamide / 120 °C
View Scheme
Multi-step reaction with 2 steps
1.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C
1.2: 24 h / 35 °C
2.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C
View Scheme
1724-17-0, 73584-64-2

oleanolic acid methyl ester

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
2.2: 24 h / 35 °C / Inert atmosphere
3.1: potassium iodide / N,N-dimethyl-formamide / 24 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
2.2: 90 °C / Inert atmosphere; Darkness
2.3: 18 h / 37 °C / Inert atmosphere
3.1: potassium iodide / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
View Scheme
Multi-step reaction with 3 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione; fluorobenzene / dimethyl sulfoxide / 24 h / 85 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 24 h / 0 - 20 °C / Inert atmosphere
2.2: 90 °C / Inert atmosphere; Darkness
3.1: potassium iodide / N,N-dimethyl-formamide / 16 h / 120 °C / Inert atmosphere
View Scheme
65023-20-3

methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate

218600-53-4

bardoxolone methyl

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: 97 percent / methanolic KOH / 0.5 h / Heating
2: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C
3: 99 percent / NaOMe / benzene / 2 h / 20 °C
4: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating
5: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C
6: 92 percent / DDQ / benzene / 0.5 h / Heating
View Scheme
Multi-step reaction with 6 steps
1: aq. KOH / methanol
2: CrO3, H2SO4
3: 100 percent / sodium methoxide / benzene
4: 61 percent / NH2OH*HCl / aq. ethanol
5: 100 percent / sodium methoxide / methanol; diethyl ether
6: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF
View Scheme
Multi-step reaction with 5 steps
1: potassium hydroxide; water / methanol
2: sodium methylate / benzene
3: hydroxylamine hydrochloride / water; ethanol
4: sodium methylate / methanol; diethyl ether
5: Phenylselenyl chloride / ethyl acetate
View Scheme
Multi-step reaction with 4 steps
1.1: potassium hydroxide / methanol / 1 h / Reflux
2.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
3.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
3.2: 0.08 h / -78 - 20 °C
4.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
View Scheme
Raw Materials
65023-20-3
65023-19-0
1724-17-0
305818-40-0
508-02-1
218600-50-1
Downstream Products
218600-44-3
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    218600-53-4

    Bardoxolone methyl

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  • high purity 218600-53-4 Methyl 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oate

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