2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid supplier

Name
Bardoxolone
EINECS
CAS No. 218600-44-3
Article Data8
CAS DataBase
Density 1.18g/cm³
Solubility
Melting Point 180-182 °C
Formula C₃₁H₄₁NO₄
Boiling Point 632.9°Cat760mmHg
Molecular Weight 491.671
Flash Point 336.6°C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms (4aS,6aR,6bS,8aS,12aR,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylic acid;
PSA 95.23000
LogP 6.29058

Synthetic route

: 218600-53-4
bardoxolone methyl

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With lithium iodide In N,N-dimethyl-formamide	71%
With lithium iodide In N,N-dimethyl-formamide	71%
With lithium iodide In N,N-dimethyl-formamide at 153℃; for 12h; Inert atmosphere;	70.3%
With lithium iodide In N,N-dimethyl-formamide for 4h; Heating;	68%
With lithium iodide In N,N-dimethyl-formamide Inert atmosphere; Reflux;	44%

: 915710-94-0, 1244059-91-3, 1165931-54-3
tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate

: 443104-14-1
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A: C39H54N4O5

B: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Stage #1: tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate; 2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere; Stage #2: With tetra(n-butyl)ammonium hydroxide In tetrahydrofuran; water at 20℃; for 5h; Inert atmosphere;	A 45% B n/a

...Expand

: 915710-94-0, 1244059-91-3, 1165931-54-3
tert‐butyl N‐[2‐(N‐hydroxycarbamimidoyl)ethyl]carbamate

: 443104-14-1
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A: C39H56N4O6

B: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h; Inert atmosphere;

...Expand

: 67015-15-0
3-methoxypropionamidoxime hydrochloride

: 443104-14-1
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

A: C35H49N3O5

B: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With triethylamine; trimethylamine In dichloromethane at 20℃; Inert atmosphere;

...Expand

: 65023-20-3
methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 7 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 7: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme
Multi-step reaction with 7 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 7: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 6 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 6: lithium iodide / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 5 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 5.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

: 218600-50-1
methyl 3,12-dioxoolean-9(11)-en-28-oate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: 99 percent / NaOMe / benzene / 2 h / 20 °C 2: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 3: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 4: 92 percent / DDQ / benzene / 0.5 h / Heating 5: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme
Multi-step reaction with 5 steps 1: 100 percent / sodium methoxide / benzene 2: 61 percent / NH2OH*HCl / aq. ethanol 3: 100 percent / sodium methoxide / methanol; diethyl ether 4: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 5: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 5 steps 1: sodium methylate / benzene 2: hydroxylamine hydrochloride / water; ethanol 3: sodium methylate / methanol; diethyl ether 4: Phenylselenyl chloride / ethyl acetate 5: lithium iodide / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 3 steps 1.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 1.2: 0.08 h / -78 - 20 °C 2.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 3.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

: 65023-19-0
methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1: 92 percent / Jones reagent / acetone / 0.17 h / 20 °C 2: 99 percent / NaOMe / benzene / 2 h / 20 °C 3: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 4: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 5: 92 percent / DDQ / benzene / 0.5 h / Heating 6: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme
Multi-step reaction with 6 steps 1: CrO3, H2SO4 2: 100 percent / sodium methoxide / benzene 3: 61 percent / NH2OH*HCl / aq. ethanol 4: 100 percent / sodium methoxide / methanol; diethyl ether 5: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 6: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 4 steps 1.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 2.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 2.2: 0.08 h / -78 - 20 °C 3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 4.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

: 218600-52-3
methyl 12-oxoisoxazolo[4,5-b]olean-9(11)-en-28-oate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 2: 92 percent / DDQ / benzene / 0.5 h / Heating 3: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme
Multi-step reaction with 3 steps 1: 100 percent / sodium methoxide / methanol; diethyl ether 2: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 3: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 3 steps 1: sodium methylate / methanol; diethyl ether 2: Phenylselenyl chloride / ethyl acetate 3: lithium iodide / N,N-dimethyl-formamide View Scheme

: 1309236-68-7
2-cyano-3-hydroxy-12-oxoolean-2(3),9(11)-dien-28-oic acid

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.25h; Reflux;	91%

: 305818-39-7
methyl 2-hydroxymethylene-3,12-dioxoolean-9(11)-en-28-oate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 66 percent / NH2OH*HCl / ethanol; H2O / 1 h / Heating 2: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 3: 92 percent / DDQ / benzene / 0.5 h / Heating 4: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

: 305818-40-0
1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 92 percent / DDQ / benzene / 0.5 h / Heating 2: 68 percent / LiI / dimethylformamide / 4 h / Heating View Scheme

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

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 2: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 2 steps 1: Phenylselenyl chloride / ethyl acetate 2: lithium iodide / N,N-dimethyl-formamide View Scheme
Multi-step reaction with 2 steps 1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 2: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

: 1309236-68-7
2-cyano-3-hydroxy-12-oxoolean-2(3),9(11)-dien-28-oic acid

A: 1309943-46-1
2-cyano-3,12-dioxooleana-1,9(11)-diene-13β,28-lactone

B: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 24h; Reflux;	A 58% B 28%

: 218600-51-2
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Formyl-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-octadecahydro-2H-picene-4a-carboxylic acid methyl ester

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: 61 percent / NH2OH*HCl / aq. ethanol 2: 100 percent / sodium methoxide / methanol; diethyl ether 3: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF 4: 71 percent / LiI / dimethylformamide View Scheme
Multi-step reaction with 4 steps 1: hydroxylamine hydrochloride / water; ethanol 2: sodium methylate / methanol; diethyl ether 3: Phenylselenyl chloride / ethyl acetate 4: lithium iodide / N,N-dimethyl-formamide View Scheme

: 508-02-1
Oleanolic acid

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 4.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 5.1: potassium hydroxide / methanol / 1 h / Reflux 6.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 7.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 7.2: 0.08 h / -78 - 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 9.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 9 steps 1.1: triethylamine; dmap / dichloromethane / 12 h / 20 °C / Inert atmosphere 2.1: potassium carbonate / acetone / 24 h / 20 °C 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 4.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 5.1: potassium hydroxide / methanol / 1 h / Reflux 6.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 7.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 7.2: 0.08 h / -78 - 20 °C 8.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 9.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 24 h / 20 °C / Inert atmosphere 2.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; fluorobenzene / 24 h / 85 °C / Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C 3.2: 24 h / 35 °C 4.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C 5.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme

: 25493-69-0, 122798-61-2, 1721-57-9
(4aS,6aS,6bR,10S,12aR)-methyl 10-acetoxy-2,2,6a,6b,9,9,12a-heptamethyl-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-icosahydropicene-4a-carboxylate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 3.1: potassium hydroxide / methanol / 1 h / Reflux 4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 5.2: 0.08 h / -78 - 20 °C 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 7 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 3.1: potassium hydroxide / methanol / 1 h / Reflux 4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 5.2: 0.08 h / -78 - 20 °C 6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 7 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C
2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C
3.1: potassium hydroxide / methanol / 1 h / Reflux
4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
5.2: 0.08 h / -78 - 20 °C
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux
View Scheme

Multi-step reaction with 7 steps
1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
2.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C
3.1: potassium hydroxide / methanol / 1 h / Reflux
4.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
5.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
5.2: 0.08 h / -78 - 20 °C
6.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
7.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux
View Scheme

: 4339-72-4
oleanolic acid 3-acetate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetone / 24 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C 3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 4.1: potassium hydroxide / methanol / 1 h / Reflux 5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 6.2: 0.08 h / -78 - 20 °C 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme
Multi-step reaction with 8 steps 1.1: potassium carbonate / acetone / 24 h / 20 °C 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C 3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 4.1: potassium hydroxide / methanol / 1 h / Reflux 5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 6.2: 0.08 h / -78 - 20 °C 7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 8 steps
1.1: potassium carbonate / acetone / 24 h / 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 0 - 20 °C
3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C
4.1: potassium hydroxide / methanol / 1 h / Reflux
5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
6.2: 0.08 h / -78 - 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux
View Scheme

Multi-step reaction with 8 steps
1.1: potassium carbonate / acetone / 24 h / 20 °C
2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 12 h / 0 - 20 °C
3.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C
4.1: potassium hydroxide / methanol / 1 h / Reflux
5.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
6.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
6.2: 0.08 h / -78 - 20 °C
7.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
8.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux
View Scheme

: 25493-94-1
methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 6 steps 1.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C 2.1: potassium hydroxide / methanol / 1 h / Reflux 3.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C 4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere 4.2: 0.08 h / -78 - 20 °C 5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere 6.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux View Scheme

Yield

Multi-step reaction with 6 steps
1.1: hydrogen bromide; bromine / acetonitrile / 19 h / 35 °C
2.1: potassium hydroxide / methanol / 1 h / Reflux
3.1: chromium(VI) oxide; sulfuric acid / water; acetone / 0 - 20 °C
4.1: lithium diisopropyl amide / tetrahydrofuran; n-heptane; ethylbenzene / 0.33 h / -78 - 20 °C / Inert atmosphere
4.2: 0.08 h / -78 - 20 °C
5.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / benzene / 0.5 h / Reflux; Inert atmosphere
6.1: lithium iodide / N,N-dimethyl-formamide / Inert atmosphere; Reflux
View Scheme

: 1724-17-0, 73584-64-2
oleanolic acid methyl ester

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; fluorobenzene / 24 h / 85 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C 2.2: 24 h / 35 °C 3.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C 4.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme

Yield

Multi-step reaction with 4 steps
1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / dimethyl sulfoxide; fluorobenzene / 24 h / 85 °C / Inert atmosphere
2.1: 3-chloro-benzenecarboperoxoic acid; hydrogen bromide / dichloromethane / 26 h / 20 °C
2.2: 24 h / 35 °C
3.1: potassium iodide / N,N-dimethyl-formamide / 30 h / 120 °C
4.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °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

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
Multi-step reaction with 3 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 3.1: lithium iodide / N,N-dimethyl-formamide / 12 h / 153 °C / Inert atmosphere View Scheme

: C31H43NO4

: 218600-44-3
bardoxolone

Conditions

Conditions	Yield
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.333333h; Reflux;

: 218600-44-3
bardoxolone

: 443104-14-1
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

Conditions

Conditions	Yield
With oxalyl dichloride In dichloromethane	100%
With oxalyl dichloride In dichloromethane at 20℃;	100%
With oxalyl dichloride In dichloromethane	100%

: 218600-44-3
bardoxolone

: 1192122-92-1
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl azide

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine at 0 - 20℃;	90%
With diphenyl phosphoryl azide; triethylamine In toluene at 20℃; for 6h;	90%

: 218600-44-3
bardoxolone

: 572-09-8
2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid (2S,3R,4S,5R,6R)-3,4,5-triacetoxy-6-acetoxymethyl-tetrahydro-pyran-2-yl ester

Conditions

Conditions	Yield
With Aliquat 336; potassium carbonate In dichloromethane	75%
With potassium carbonate; Aliquat 336 In dichloromethane; water	75%

: 218600-44-3
bardoxolone

: 1191917-53-9
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl fluoride

Conditions

Conditions	Yield
With diethylamino-sulfur trifluoride In chloroform at 20℃; for 6.5h;	94%

: 218600-44-3
bardoxolone

: C31H41NO5

Conditions

Conditions	Yield
With dihydrogen peroxide In methanol; water; acetonitrile at 20℃; for 30h;	90%

: 67-56-1
methanol

: 218600-44-3
bardoxolone

: 218600-53-4
bardoxolone methyl

Conditions

Conditions	Yield
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%

: O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

: 218600-44-3
bardoxolone

: O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(piperidine-1-yl)diazen-1-ium-1,2-diolate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 45℃; for 4h;	68%

: O2-(2,4-dinitro-5-(2-bromoethylamino)phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

: 218600-44-3
bardoxolone

: O2-(2,4-dinitro-5-{2-[2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oyl]-oxoethylamino}phenyl)-1-(N-methylethanolamino)diazen-1-ium-1,2-diolate

Conditions

Conditions	Yield
With potassium carbonate In acetone at 45℃; for 4h;	74%

: 218600-44-3
bardoxolone

: C31H43NO4

Conditions

Conditions	Yield
With palladium 10% on activated carbon; hydrogen In tetrahydrofuran	84%

: 80841-78-7
4-chloromethyl-5-methyl-1,3-dioxol-2-one

: 218600-44-3
bardoxolone

: C36H45NO7

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating / reflux;	83%

: 79-03-8
propionyl chloride

: 16106-20-0, 16908-90-0, 16908-91-1, 35993-37-4, 38709-03-4, 114718-64-8, 127001-76-7, 16051-77-7
isosorbide mononitrate

: 218600-44-3
bardoxolone

: 1-isosorbide mononitrate 2-cyano-3-propionyloxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

Conditions

Conditions	Yield
Stage #1: isosorbide mononitrate; bardoxolone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: propionyl chloride In N,N-dimethyl-formamide	35%

...Expand

: 16106-20-0, 16908-90-0, 16908-91-1, 35993-37-4, 38709-03-4, 114718-64-8, 127001-76-7, 16051-77-7
isosorbide mononitrate

: 75-36-5
acetyl chloride

: 218600-44-3
bardoxolone

: 1-isosorbide mononitrate 2-cyano-3-acetoxy-12-oxoolean-2(3),9(11)-diene-28-carboxylic acid

Conditions

Conditions	Yield
Stage #1: isosorbide mononitrate; bardoxolone With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: acetyl chloride In N,N-dimethyl-formamide for 6h;	35%

...Expand

: 218600-44-3
bardoxolone

: 1192122-95-4
(4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-isocyanato-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile

Conditions

Conditions	Yield
Stage #1: bardoxolone With diphenyl phosphoryl azide; triethylamine In toluene at 0 - 20℃; Stage #2: In benzene at 80℃; for 2h;
Multi-step reaction with 2 steps 1: diphenyl phosphoryl azide; triethylamine / 0 - 20 °C 2: benzene / 2 h / 80 °C View Scheme

: 218600-44-3
bardoxolone

A: 1192122-92-1
(4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-octadecahydropicene-4a-carbonyl azide

B: 1192122-95-4
(4aR,6aS,6bR,8aS,12aS,12bR,14bS)-8a-isocyanato-4,4,6a,6b,11,11,14b-heptamethyl-3,13-dioxo-3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,12b,13,14b-octadecahydropicene-2-carbonitrile

Conditions

Conditions	Yield
With diphenyl phosphoryl azide; triethylamine In toluene at 0 - 20℃; Overall yield = 94 %; Overall yield = 19.7 g;

: 218600-44-3
bardoxolone

: 359860-27-8
N-(2-(2-(2-(2-amidoethoxy)ethoxy)ethoxy)ethoxy)biotinamide

: 11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid {2-[2-(2-{2-[5-(2-oxo-hexahydro-thieno[3,4-d]imidazol-6-yl)-pentanoylamino]-ethoxy}-ethoxy)-ethoxy]-ethyl}-amide

Conditions

Conditions	Yield
With 2`,3`-dideoxycytidine; dmap In dichloromethane at 20℃; for 48h;	79%

: 218600-44-3
bardoxolone

: 443104-14-1
2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid chloride

: 1224947-97-0
2-cyano-3,10-dioxooleana-1,9(11)-dien-28-oic acid anhydride

Conditions

Conditions	Yield
With triethylamine In tetrahydrofuran at 20℃; for 1.5h;	96%

: 218600-44-3
bardoxolone

benzyl halide: benzyl halide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid benzyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;	97%

: 218600-44-3
bardoxolone

ethyl halide: ethyl halide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;	100%

: 218600-44-3
bardoxolone

n-octyl halide: n-octyl halide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid octyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;	89%

: 218600-44-3
bardoxolone

cyclopropylmethyl halide: cyclopropylmethyl halide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid cyclopropylmethyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;	81%

: 218600-44-3
bardoxolone

n-butyl halide: n-butyl halide

: (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-Cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,6a,6b,7,8,8a,9,10,12a,14,14a,14b-hexadecahydro-2H-picene-4a-carboxylic acid butyl ester

Conditions

Conditions	Yield
With 1,8-diazabicyclo[5.4.0]undec-7-ene In toluene Heating;	74%

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid Specification

The 2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid with the cas number 218600-44-3 is also called CDDO acid. The IUPAC name is (4aS,6aR,6bS,8aR,12aS,14aR,14bS)-11-cyano-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,3,4,5,6,7,8,8a,14a,14b-decahydropicene-4a-carboxylic acid. Its molecular formula is C₃₁H₄₁NO₄. This chemical is a kind of organics. It should be stored in dry and cool environment.

The properties of the chemical are: (1)ACD/LogP: 5.76; (2)# of Rule of 5 Violations: 1 ; (3)#H bond acceptors: 5; (4)#H bond donors: 1; (5)#Freely Rotating Bonds: 1; (6)Polar Surface Area: 84.23Å²; (7)Index of Refraction: 1.574; (8)Molar Refractivity: 136.54 cm³; (9)Molar Volume: 413.4 cm³; (10)Polarizability: 54.13×10^-24cm³; (11)Surface Tension: 51.1 dyne/cm; (12)Enthalpy of Vaporization: 102.11 kJ/mol; (13)Vapour Pressure: 1.2×10^-17 mmHg at 25°C.

You can still convert the following datas into molecular structure:
(1)SMILES: O=C4C(\C#N)=C/[C@@]5(/C3=C/C(=O)[C@H]2[C@](CC[C@@]1(C(=O)O)CCC(C)(C)C[C@H]12)(C)[C@]3(C)CC[C@H]5C4(C)C)C
(2)InChI: InChI=1/C31H41NO4/c1-26(2)10-12-31(25(35)36)13-11-30(7)23(19(31)16-26)20(33)14-22-28(5)15-18(17-32)24(34)27(3,4)21(28)8-9-29(22,30)6/h14-15,19,21,23H,8-13,16H2,1-7H3,(H,35,36)/t19-,21-,23-,28-,29+,30+,31-/m0/s1
(3)InChIKey: TXGZJQLMVSIZEI-UQMAOPSPBH

Product Name

Bardoxolone

Synthetic route

2-Cyano-3,12-dioxooleana-1,9-dien-28-oic acid Specification

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