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inquiryOleana-1,9(11)-dien-28-oicacid, 2-cyano-3,12-dioxo-, methyl esterAppearance:white crystalline powder Storage:Store in dry, dark and ventilated place Package:25KG drum Application:pharmaceutical intermediate Transportation:by air, by sea, by express
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2-bromo-3,12-dioxo-oleanane-1,9 (11)-diene-28-carboxylic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
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% |
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% |
bardoxolone methyl
Conditions | Yield |
---|---|
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; |
Conditions | Yield |
---|---|
With potassium iodide In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere; | 89% |
1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.5h; Heating; | 92% |
bardoxolone methyl
Conditions | Yield |
---|---|
With porcine liver esterase; γ-glutamyl transpeptidase In aq. buffer at 37℃; for 8h; pH=7.4; Enzymatic reaction; | 88% |
Oleanolic acid
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
oleanolic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
methyl 3,12-dioxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 View Scheme | |
Multi-step reaction with 4 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 View Scheme | |
Multi-step reaction with 4 steps 1: sodium methylate / benzene 2: hydroxylamine hydrochloride / water; ethanol 3: sodium methylate / methanol; diethyl ether 4: Phenylselenyl chloride / ethyl acetate View Scheme | |
Multi-step reaction with 2 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 View Scheme |
methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 3 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 View Scheme |
methyl 12-oxoisoxazolo[4,5-b]olean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 2: 92 percent / DDQ / benzene / 0.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 100 percent / sodium methoxide / methanol; diethyl ether 2: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF View Scheme |
methyl 2-hydroxymethylene-3,12-dioxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme | |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / water; ethanol 2: sodium methylate / methanol; diethyl ether 3: Phenylselenyl chloride / ethyl acetate View Scheme |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 6 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 View Scheme | |
Multi-step reaction with 6 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 View Scheme |
oleanolic acid 3-acetate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 7 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 View Scheme | |
Multi-step reaction with 7 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 View Scheme |
methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme |
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% |
1,2-dihydro-2-cyano-3,12-dioxooleana-1,9(11)-dien-28-oic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
With 2,3-dicyano-5,6-dichloro-p-benzoquinone In benzene for 0.5h; Heating; | 92% |
Conditions | Yield |
---|---|
With potassium iodide In N,N-dimethyl-formamide at 120℃; for 16h; Inert atmosphere; | 89% |
bardoxolone methyl
Conditions | Yield |
---|---|
With porcine liver esterase; γ-glutamyl transpeptidase In aq. buffer at 37℃; for 8h; pH=7.4; Enzymatic reaction; | 88% |
bardoxolone methyl
Conditions | Yield |
---|---|
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; |
2-bromo-3,12-dioxo-oleanane-1,9 (11)-diene-28-carboxylic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
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% |
methyl 3β-hydroxy-12-oxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 5 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 View Scheme | |
Multi-step reaction with 3 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 View Scheme |
methyl 3β-acetoxy-12-oxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
methyl 3,12-dioxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 4 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 View Scheme | |
Multi-step reaction with 4 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 View Scheme | |
Multi-step reaction with 4 steps 1: sodium methylate / benzene 2: hydroxylamine hydrochloride / water; ethanol 3: sodium methylate / methanol; diethyl ether 4: Phenylselenyl chloride / ethyl acetate View Scheme | |
Multi-step reaction with 2 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 View Scheme |
methyl 12-oxoisoxazolo[4,5-b]olean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 100 percent / NaOMe / methanol; diethyl ether / 0.75 h / 20 °C 2: 92 percent / DDQ / benzene / 0.5 h / Heating View Scheme | |
Multi-step reaction with 2 steps 1: 100 percent / sodium methoxide / methanol; diethyl ether 2: 1.) phenylselenenyl chloride, 2.) 30 percent aq. H2O2 / 1.) ethyl acetate, 2.) THF View Scheme |
methyl 2-hydroxymethylene-3,12-dioxoolean-9(11)-en-28-oate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 3 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 View Scheme | |
Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride / water; ethanol 2: sodium methylate / methanol; diethyl ether 3: Phenylselenyl chloride / ethyl acetate View Scheme |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
Oleanolic acid
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
oleanolic acid methyl ester
bardoxolone methyl
Conditions | Yield |
---|---|
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 |
(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
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 6 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 View Scheme | |
Multi-step reaction with 6 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 View Scheme |
methyl 3-O-β-acetyl-11-dehydro-12-oxo-18β-oleanolate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 5 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 View Scheme |
oleanolic acid 3-acetate
bardoxolone methyl
Conditions | Yield |
---|---|
Multi-step reaction with 7 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 View Scheme | |
Multi-step reaction with 7 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 View Scheme |
bardoxolone methyl
Conditions | Yield |
---|---|
With 3-chloro-benzenecarboperoxoic acid In dichloromethane at 20℃; for 3h; Cooling with ice; | 99% |
With dihydrogen peroxide In water; acetonitrile at 20℃; for 48h; | 92% |
With iodosylbenzene In chloroform for 12h; Inert atmosphere; | 75% |
benzyl bromide
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: bardoxolone methyl With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: benzyl bromide In water; N,N-dimethyl-formamide at 20℃; for 2h; Inert atmosphere; | 84% |
bardoxolone methyl
bardoxolone
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% |
bardoxolone methyl
(4aS,6aR,6bS,8aR,11R,12R,12aS,14aR,14bS)-methyl-11-cyano-11,12-dihydroxy-2,2,6a,6b,9,9,12a-heptamethyl-10,14-dioxo-1,2,3,4,4a,5,6,6a,6b,7,8,8a,9,10,11,12,12a,14,14a,14b-icosahydropicene-4a-carboxylate
Conditions | Yield |
---|---|
With sodium periodate; (x)ClH*Cl3Ru In water; ethyl acetate; acetonitrile at 0℃; for 0.0833333h; | 71% |
methanol
4-bromomethylphenylboronic acid pinacol ester
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: methanol; bardoxolone methyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-bromomethylphenylboronic acid pinacol ester In N,N-dimethyl-formamide for 0.5h; | 67% |
bardoxolone methyl
Conditions | Yield |
---|---|
With iodosylbenzene In chloroform at 20℃; for 16h; | 62% |
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: bardoxolone methyl With potassium carbonate In water; N,N-dimethyl-formamide at 20℃; Inert atmosphere; Stage #2: methyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N5-(4-(bromomethyl)phenyl)-L-glutaminate In water; N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; | 61% |
Stage #1: bardoxolone methyl With water; potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: methyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N5-(4-(bromomethyl)phenyl)-L-glutaminate In N,N-dimethyl-formamide for 0.5h; | 53% |
Conditions | Yield |
---|---|
Stage #1: bardoxolone methyl With water; potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-bromomethylphenylboronic acid pinacol ester In N,N-dimethyl-formamide for 0.5h; | 53% |
ethanol
4-bromomethylphenylboronic acid pinacol ester
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: ethanol; bardoxolone methyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: 4-bromomethylphenylboronic acid pinacol ester In N,N-dimethyl-formamide for 0.5h; | 49% |
ethanol
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: ethanol; bardoxolone methyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: methyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N5-(4-(bromomethyl)phenyl)-L-glutaminate In N,N-dimethyl-formamide for 0.5h; | 39% |
methanol
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: methanol; bardoxolone methyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: methyl N2-(((9H-fluoren-9-yl)methoxy)carbonyl)-N5-(4-(bromomethyl)phenyl)-L-glutaminate In N,N-dimethyl-formamide for 0.5h; | 38% |
Conditions | Yield |
---|---|
Stage #1: isosorbide mononitrate; bardoxolone methyl With potassium carbonate In N,N-dimethyl-formamide at 20℃; Stage #2: acetyl chloride In N,N-dimethyl-formamide for 6h; | 35% |
Conditions | Yield |
---|---|
With lithium diisopropyl amide In tetrahydrofuran at -78℃; Inert atmosphere; | 16% |
bardoxolone methyl
Conditions | Yield |
---|---|
Stage #1: bardoxolone methyl With N-bromosaccharin; water In acetonitrile at 20℃; for 2h; Stage #2: With triethylamine In benzene at 20℃; for 1h; | 4.9% |
bardoxolone methyl
benzene
Conditions | Yield |
---|---|
In acetone for 0.666667h; Ultrasonic processor; |
methanol
bardoxolone methyl
Conditions | Yield |
---|---|
at -10 - 60℃; | |
at -15 - 60℃; Product distribution / selectivity; Industry scale; |
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