Conditions | Yield |
---|---|
With methanol; sodium methylate at 25℃; for 4h; | 90% |
Conditions | Yield |
---|---|
With hydrogen fluoride In water; N,N-dimethyl-formamide at -15℃; | 89% |
With hydrogen fluoride |
betamethasone
Conditions | Yield |
---|---|
Stage #1: C24H31FO5 In ethyl acetate at 0 - 10℃; Stage #2: With hydrogenchloride In water at 30 - 35℃; for 1h; | 45% |
betamethasone dipropionate
A
betamethasone
B
Betamethasone propionate
C
6β-hydroxybetamethasone
D
6β-hydroxybetamethasone 17-propionate
Conditions | Yield |
---|---|
With phosphate buffer; air; plasma of 20 d pregnant Sprague-Dawley rat at 37℃; for 1h; Product distribution; metabolism with tissues (plasma, liver, brain, placenta) from mothers and fetuses of Sprague-Dawley rats sacrificed on day 20 of pregnancy and mice on day 17 of pregnancy, further in vivo; | A 14.8 % Chromat. B 67.8 % Chromat. C 1.4 % Chromat. D 2.3 % Chromat. |
betamethasone
Conditions | Yield |
---|---|
With sodium methylate |
Conditions | Yield |
---|---|
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures; |
16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: 95 percent / pyridine / 20 °C 2.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 3.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 4.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 4.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 5.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 5.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 6.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 7.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 8.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 9.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 2: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 3: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 4: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 1.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 2.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 2.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 3.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 4.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 5.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 6.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 2.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 2.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 3.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 3.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 4.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 5.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 6.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 7.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
(8S,9R,10S,11S,13S,14S,16S,17R)-17-(2,2-Diiodo-acetyl)-9-fluoro-11,17-dihydroxy-10,13,16-trimethyl-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-cyclopenta[a]phenanthren-3-one
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 2: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 1.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 2.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 3.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 4.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 5.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 2.1: 95 percent / pyridine / 20 °C 3.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 4.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 5.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 5.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 6.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 6.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 7.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 8.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 9.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 10.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 11 steps 1.1: pyridine; ammonium chloride / 125 - 135 °C 1.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 1.3: 57 percent / aluminium oxide / benzene / 2 h 2.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 3.1: 95 percent / pyridine / 20 °C 4.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 5.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 6.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 6.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 7.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 7.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 8.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 9.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 10.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 11.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
3β-acetoxy-16α,17α-epoxy-5α-pregn-9(11)-en-20-one
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 2.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 3.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 3.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 4.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 4.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 5.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 6.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 7.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 8.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 12 steps 1.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 1.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 2.1: pyridine; ammonium chloride / 125 - 135 °C 2.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 2.3: 57 percent / aluminium oxide / benzene / 2 h 3.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 4.1: 95 percent / pyridine / 20 °C 5.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 6.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 7.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 7.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 8.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 9.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 10.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 11.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 12.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 2: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 3: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 14 steps 1.1: 95 percent / pyridine / 20 °C 2.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 3.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 3.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 4.1: pyridine; ammonium chloride / 125 - 135 °C 4.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 4.3: 57 percent / aluminium oxide / benzene / 2 h 5.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 6.1: 95 percent / pyridine / 20 °C 7.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 8.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 9.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 9.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 10.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 10.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 11.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 12.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 13.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 14.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 13 steps 1.1: 72 percent / m-iodoxybenzoic acid; diphenyl diselenide / toluene / 12 h / Heating 2.1: hydrazine hydrate / ethane-1,2-diol / 1 h / Heating 2.2: 95 percent / potassium hydroxide / ethane-1,2-diol; H2O / 5 h / 195 - 197 °C 3.1: pyridine; ammonium chloride / 125 - 135 °C 3.2: acetic acid; chromium trioxide / H2O; 1,2-dichloro-ethane / 1 h / 20 °C 3.3: 57 percent / aluminium oxide / benzene / 2 h 4.1: 91.7 percent / hydrogen peroxide; sodium hydroxide / methanol / 2 h / 20 °C 5.1: 95 percent / pyridine / 20 °C 6.1: 70 percent / triethyl orthoformate; p-toluenesulfonic acid / CH2Cl2 / 20 h / 20 °C 7.1: 72 percent / tetrahydrofuran; diethyl ether / 72 h / 60 °C 8.1: m-iodoxybenzoic acid; diphenyl diselenide / toluene / 22 h / Heating 8.2: 50 percent / p-toluenesulfonic acid / CH2Cl2 / 4 h / 20 °C 9.1: perchloric acid; 1,3-dibromo-5,5-dimethylhydantoin / dimethylformamide / 3 h / cooling 9.2: 75.8 percent / sodium hydroxide / CH2Cl2; methanol; H2O / 2 h / cooling 10.1: 80 percent / hydrofluoric acid / tetrahydrofuran; CH2Cl2 / 5 h / -70 - 0 °C 11.1: 100 percent / anhydrous calcium chloride; calcium oxide; iodine / methanol / 1 h / 25 - 27 °C 12.1: 180 mg / acetic acid / acetone; H2O / 3 h / Heating 13.1: 90 percent / sodium methoxide; methanol / 4 h / 25 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 2.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 3.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 3.2: 0 - 5 °C 4.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 5.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 6.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 7.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 2.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 2.2: 0 - 5 °C 3.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 4.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 5.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 6.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 1.2: 0 - 5 °C 2.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 3.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 4.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 5.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 2: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 3: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 4: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
21-acetyloxy-17α-hydroxy-16β-methylpregna-4,9(11)-diene-3,20-dione
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 2: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 3: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 2: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid / ethanol / 4 h / 40 °C / Inert atmosphere 2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium diisopropyl amide / tetrahydrofuran; hexane / 3 h / -40 - 20 °C / Inert atmosphere 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 3.2: 5 h / -45 - 20 °C / Inert atmosphere 4.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 6.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 6.2: 0 - 5 °C 7.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 9.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 10.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid / ethanol / 4 h / 40 °C / Inert atmosphere 2.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide / tetrahydrofuran / -40 - 20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 3.2: 5 h / -45 - 20 °C / Inert atmosphere 4.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 6.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 6.2: 0 - 5 °C 7.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 9.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 10.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme | |
Multi-step reaction with 10 steps 1.1: toluene-4-sulfonic acid / ethanol / 4 h / 40 °C / Inert atmosphere 2.1: potassium tert-butylate / tetrahydrofuran / -20 °C 3.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 3.2: 5 h / -45 - 20 °C / Inert atmosphere 4.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 5.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 6.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 6.2: 0 - 5 °C 7.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 8.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 9.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 10.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 9 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; n-butyllithium; lithium diisopropyl amide / tetrahydrofuran; hexane / 3 h / -40 - 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 2.2: 5 h / -45 - 20 °C / Inert atmosphere 3.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 5.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 5.2: 0 - 5 °C 6.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 7.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 8.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 9.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: N,N,N,N,N,N-hexamethylphosphoric triamide; lithium diisopropyl amide / tetrahydrofuran / -40 - 20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 2.2: 5 h / -45 - 20 °C / Inert atmosphere 3.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 5.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 5.2: 0 - 5 °C 6.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 7.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 8.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 9.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme | |
Multi-step reaction with 9 steps 1.1: potassium tert-butylate / tetrahydrofuran / -20 °C 2.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 2.2: 5 h / -45 - 20 °C / Inert atmosphere 3.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 4.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 5.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 5.2: 0 - 5 °C 6.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 7.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 8.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 9.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / 0.75 h / -45 - -30 °C / Inert atmosphere 1.2: 5 h / -45 - 20 °C / Inert atmosphere 2.1: alkali metal acetate / N,N-dimethyl-formamide / 2 h / 115 °C / Inert atmosphere 3.1: 3-chloro-benzenecarboperoxoic acid / dichloromethane / 6 h / -5 - 0 °C 4.1: hydrogen bromide / 1,4-dioxane / 5 h / 35 °C 4.2: 0 - 5 °C 5.1: Wilkinson's catalyst; hydrogen / ethyl acetate / 60 - 65 °C / 760.05 Torr 6.1: perchloric acid; 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione / water; acetone / 2.5 h / 0 - 5 °C 7.1: D-Glucose / aq. phosphate buffer / 76 h / Microbiological reaction 8.1: hydrogen fluoride / water; N,N-dimethyl-formamide / -15 °C View Scheme |
betamethasone
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1.1: potassium borohydride; ethanol / dichloromethane / 0.5 h / 0 - 10 °C 2.1: phthalic acid peroxide; peroxide phthalic anhydride / ethyl acetate / 0 - 10 °C 2.2: 1 h / 30 - 35 °C View Scheme |
Conditions | Yield |
---|---|
Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid; betamethasone With dmap In dichloromethane; N,N-dimethyl-formamide Stage #2: In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice; | 100% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water; N,N-dimethyl-formamide at 20℃; Cooling with ice; | 3.18 g |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice; | 100% |
Conditions | Yield |
---|---|
With dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice; | 99% |
Conditions | Yield |
---|---|
With dmap In N,N-dimethyl-formamide at 20℃; Cooling with ice; | 99% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; | 99% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 98% |
betamethasone
9α-fluoro-11β,17α-dihydroxy-16β-methyl-3-oxo-androsta-1,4-diene-17β-carboxylic acid
Conditions | Yield |
---|---|
With periodic acid In methanol; water at 20℃; for 16h; | 97% |
In tetrahydrofuran; water | |
In tetrahydrofuran; water | |
With periodic acid In methanol |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature; | 96% |
betamethasone
Conditions | Yield |
---|---|
With pyridine; dichlorohydantoin; sulfur dioxide In N,N-dimethyl-formamide at 5℃; for 2h; | 95.6% |
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 8h; | 95% |
N-Methylhydroxylamine
betamethasone
9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-3-methylimino-1,4-pregnadien-20-one N-oxide
Conditions | Yield |
---|---|
With pyridine at 40℃; | 87% |
Conditions | Yield |
---|---|
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 87% |
N-(tert-butyloxycarbonyl)-L-isoleucine
betamethasone
Conditions | Yield |
---|---|
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water; N,N-dimethyl-formamide at 0 - 20℃; | 87% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In benzene for 4h; Heating; | 85% |
Conditions | Yield |
---|---|
With hydrogenchloride In chloroform at 30℃; for 3h; Temperature; | 84.4% |
Conditions | Yield |
---|---|
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 82% |
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water; N,N-dimethyl-formamide at 0 - 20℃; | 82% |
betamethasone
Conditions | Yield |
---|---|
With bithmuth(III) triflate hydrate In 1,4-dioxane at 80℃; chemoselective reaction; | 68% |
betamethasone
(aminooxy)acetic acid hemihydrochloride
betamethasome-3-(O-carboxymethy)oxime
Conditions | Yield |
---|---|
With pyridine In ethanol for 8h; Ambient temperature; | 55% |
Conditions | Yield |
---|---|
With sodium hydride In benzene for 24h; Cyclocondensation; | 50% |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid; trichloroacetic acid In dichloromethane at 20℃; | 49% |
Conditions | Yield |
---|---|
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; | 18% |
6-Aminopenicillanic Acid
betamethasone
chloroformic acid ethyl ester
6β-(9-fluoro-11β,17-dihydroxy-16β-methyl-3,20-dioxo-pregna-1,4-dien-21-yloxycarbonylamino)-penicillanic acid
Conditions | Yield |
---|---|
(i) Et3N, THF, (ii) /BRN= 15080/, aq. KHCO3; Multistep reaction; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature; |
1,1,1-trimethoxybutane
betamethasone
9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17-butyrate
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Ambient temperature; |
Conditions | Yield |
---|---|
With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Ambient temperature; |
The Betamethasone is an organic compound with the formula C22H29FO5. The IUPAC name of this chemical is (8S,9R,10S,11S,13S,14S,16S,17R)-9-fluoro-11,17-dihydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,11,12,14,15,16-octahydrocyclopenta[a]phenanthren-3-one. With the CAS registry number 378-44-9, it is also named as (11β,16α)-9-Fluor-11,17,21-trihydroxy-16-methylpregna-1,4-dien-3,20-dion. The product's categories are Biochemistry; Hydroxyketosteroids; Steroids; Intermediates & Fine Chemicals; Pharmaceuticals. Besides, it is a white to off-white solid.
The Betamethasone is a corticosteroid used as a topical cream to relieve skin irritation, such as itching and flaking from eczema. Betamethasone dipropionate and salicylic acid can be used as a treatment for local psoriasis. Betamethasone is also used to stimulate fetal lung maturation (prevention of IRDS), and to decrease the incidence and mortality from intracranial hemorrhage in premature infants.
Physical properties about Betamethasone are: (1)ACD/LogP: 1.87; (2)ACD/LogD (pH 5.5): 1.87; (3)ACD/LogD (pH 7.4): 1.87; (4)ACD/BCF (pH 5.5): 15.49; (5)ACD/BCF (pH 7.4): 15.49; (6)ACD/KOC (pH 5.5): 247.46; (7)ACD/KOC (pH 7.4): 247.45; (8)#H bond acceptors: 5; (9)#H bond donors: 3; (10)#Freely Rotating Bonds: 5; (11)Polar Surface Area: 61.83 Å2; (12)Index of Refraction: 1.591; (13)Molar Refractivity: 100.23 cm3; (14)Molar Volume: 296.2 cm3; (15)Polarizability: 39.73×10-24cm3; (16)Surface Tension: 56.5 dyne/cm; (17)Density: 1.32 g/cm3; (18)Flash Point: 297.5 °C; (19)Enthalpy of Vaporization: 97.96 kJ/mol; (20)Boiling Point: 568.2 °C at 760 mmHg; (21)Vapour Pressure: 2.81E-15 mmHg at 25°C.
When you are using this chemical, please be cautious about it as the following:
This chemical has limited evidence of a carcinogenic effect. When you are using it, wear suitable protective clothing and do not breathe dust.
You can still convert the following datas into molecular structure:
(1)SMILES: O=C(CO)[C@]3(O)[C@]2(C[C@H](O)[C@]4(F)[C@@]/1(\C(=C/C(=O)\C=C\1)CC[C@H]4[C@@H]2C[C@H]3C)C)C
(2)InChI: InChI=1/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
(3)InChIKey: UREBDLICKHMUKA-CXSFZGCWBM
(4)Std. InChI: InChI=1S/C22H29FO5/c1-12-8-16-15-5-4-13-9-14(25)6-7-19(13,2)21(15,23)17(26)10-20(16,3)22(12,28)18(27)11-24/h6-7,9,12,15-17,24,26,28H,4-5,8,10-11H2,1-3H3/t12-,15+,16+,17+,19+,20+,21+,22+/m1/s1
(5)Std. InChIKey: UREBDLICKHMUKA-CXSFZGCWSA-N
The toxicity data is as follows:
Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
---|---|---|---|---|---|
mouse | LD50 | oral | > 4500mg/kg (4500mg/kg) | Gekkan Yakuji. Pharmaceuticals Monthly. Vol. 21, Pg. 2117, 1979. |
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