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378-44-9

Basic Information
CAS No.: 378-44-9
Name: Betamethasone
Molecular Structure:
Molecular Structure of 378-44-9 (Betamethasone)
Formula: C22H29FO5
Molecular Weight: 434.50
Synonyms: Celestene;Prestwick_703;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;Rinderon A;Cidoten;beta-Methasone alcohol;Betamethazone;Bedifos;Pregna-1,4-diene-3,20-dione, 9-fluoro-11,17, 21-trihydroxy-16-methyl-, (11.beta.,16.beta.)-;9.alpha.-Fluoro-16.beta.-methylprednisolone;Desacort-beta;Betsolan;Sch 4831;.beta.-Methasone alcohol;Pregna-1,4-diene-3,20-dione,9-fluoro-11,17,- 21-trihydroxy-16-methyl-,(11a,16a)-;Becort;Betacortril;Prednisolone, 9-fluoro-16beta-methyl-;Betamamallet;Betamethasone (JP14/USP);9-alpha-Fluoro-16-beta-methylprednisolone;Betafluorene;9-Fluoro-11-beta,17,21-trihydroxy-16-beta-methylpregna-1,4-diene-3,20-dione;Betapredol;Visubeta;
EINECS: 206-825-4
Density: 1.32 g/cm3
Melting Point: 235-237 °C
Boiling Point: 568.2 °C at 760 mmHg
Flash Point: 297.5 °C
Solubility:
Appearance: white to off-white solid
Hazard Symbols: IrritantXi,HarmfulXn
Risk Codes: 40
Safety: 22-36
Transport Information:
PSA: 94.83000
LogP: 1.89570
Synthetic route
987-24-6

betamethasone 21-acetate

378-44-9

betamethasone

Conditions
ConditionsYield
With methanol; sodium methylate at 25℃; for 4h;90%
981-34-0

17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
With hydrogen fluoride In water; N,N-dimethyl-formamide at -15℃;89%
With hydrogen fluoride

C24H31FO5

378-44-9

betamethasone

Conditions
ConditionsYield
Stage #1: C24H31FO5 In ethyl acetate at 0 - 10℃;
Stage #2: With hydrogenchloride In water at 30 - 35℃; for 1h;
45%
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

24703-00-2

6β-hydroxybetamethasone

D

78144-00-0

6β-hydroxybetamethasone 17-propionate

Conditions
ConditionsYield
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.
21-acetoxy-9-fluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione/s

21-acetoxy-9-fluoro-11,17-dihydroxy-16-methyl-pregna-1,4-diene-3,20-dione/s

378-44-9

betamethasone

Conditions
ConditionsYield
With sodium methylate
5593-20-4

betamethasone dipropionate

A

378-44-9

betamethasone

B

5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

Conditions
ConditionsYield
With sulfuric acid In acetonitrile at 20℃; for 20h; Product distribution; Further Variations:; Temperatures;
884488-47-5

16α,17α-epoxy-3β-hydroxy-5α-pregn-9(11)-en-20-one

378-44-9

betamethasone

Conditions
ConditionsYield
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
37413-99-3

16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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
884488-49-7

16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

378-44-9

betamethasone

Conditions
ConditionsYield
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
884488-48-6

3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene

378-44-9

betamethasone

Conditions
ConditionsYield
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
37414-01-0

(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

378-44-9

betamethasone

Conditions
ConditionsYield
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
14135-32-1

16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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
21650-83-9

20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate

378-44-9

betamethasone

Conditions
ConditionsYield
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
1106-20-3

Δ9(11)22-isoallospirosten-3β-ol

378-44-9

betamethasone

Conditions
ConditionsYield
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
113926-56-0

3β-acetoxy-16α,17α-epoxy-5α-pregn-9(11)-en-20-one

378-44-9

betamethasone

Conditions
ConditionsYield
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
989-73-1

Δ9(11)22-isoallospirosten-3β-ol-12-one-3-acetate

378-44-9

betamethasone

Conditions
ConditionsYield
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
1879-77-2

16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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
467-55-0

hecogenin

378-44-9

betamethasone

Conditions
ConditionsYield
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
915-35-5

hecogenin acetate

378-44-9

betamethasone

Conditions
ConditionsYield
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

20-chloro-3-keto-16α-methylpregna-4,9(11),17(20)-triene-21-al

378-44-9

betamethasone

Conditions
ConditionsYield
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

21-acetoxy-16-methylpregna-4,9(11),16-triene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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

21-acetoxy-16(17)α-epoxy-16-methylpregna-4,9(11)-diene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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

21-acetoxy-17α-hydroxy-16-methylenepregna-4,9(11)-diene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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
18762-17-9

21-acetyloxy-17α-hydroxy-16β-methylpregna-4,9(11)-diene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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

21-acetoxy-17α-hydroxy-9β,11β-epoxy-16β-methylpregna-4-ene-3,20-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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
1035-69-4

androst-4,9(11)-dien-3,17-dione

378-44-9

betamethasone

Conditions
ConditionsYield
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

3-ethoxyandrosta-3,5,9(11)-diene-17-one

378-44-9

betamethasone

Conditions
ConditionsYield
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

3-ethoxy-16α-methylandrosta-3,5,9(11)-diene-17-one

378-44-9

betamethasone

Conditions
ConditionsYield
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

C24H29FO5

378-44-9

betamethasone

Conditions
ConditionsYield
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
3303-84-2

3-(tert-butyloxycarbonylamino)propionic acid

378-44-9

betamethasone

Boc-β-alanine-betamethasone

Conditions
ConditionsYield
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

C8H14ClNO4

378-44-9

betamethasone

C30H41ClFNO8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;100%

Fmoc-Orn(Boc)-OH

378-44-9

betamethasone

C47H57FN2O10

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;99%

3-[(tert-butoxycarbonyl)amino]-2-fluoropropanoic acid

378-44-9

betamethasone

C30H41F2NO8

Conditions
ConditionsYield
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%
15761-38-3

L-N-Boc-Ala

378-44-9

betamethasone

21-Boc-alanyl-betamethasone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;98%
378-44-9

betamethasone

37926-75-3

9α-fluoro-11β,17α-dihydroxy-16β-methyl-3-oxo-androsta-1,4-diene-17β-carboxylic acid

Conditions
ConditionsYield
With periodic acid In methanol; water at 20℃; for 16h;97%
In tetrahydrofuran; water
In tetrahydrofuran; water
With periodic acid In methanol
378-44-9

betamethasone

78-39-7

Triethyl orthoacetate

5534-12-3

betamethasone 17-acetate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;96%
378-44-9

betamethasone

clobetasol

Conditions
ConditionsYield
With pyridine; dichlorohydantoin; sulfur dioxide In N,N-dimethyl-formamide at 5℃; for 2h;95.6%

C8H14BrNO4

378-44-9

betamethasone

C30H41BrFNO8

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃; for 8h;95%
593-77-1

N-Methylhydroxylamine

378-44-9

betamethasone

84871-37-4

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-3-methylimino-1,4-pregnadien-20-one N-oxide

Conditions
ConditionsYield
With pyridine at 40℃;87%
13139-16-7

N-(t-butoxycarbonyl)-isoleucine

378-44-9

betamethasone

C33H48FNO8

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

378-44-9

betamethasone

21-(Boc-isoleucyl)-betamethasone

Conditions
ConditionsYield
With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane; water; N,N-dimethyl-formamide at 0 - 20℃;87%
378-44-9

betamethasone

85610-79-3

1-(13-cis-Retinoyl)imidazole

C43H53FO7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In benzene for 4h; Heating;85%
50-00-0

formaldehyd

378-44-9

betamethasone

C24H31FO6

Conditions
ConditionsYield
With hydrogenchloride In chloroform at 30℃; for 3h; Temperature;84.4%
4530-20-5

BOC-glycine

378-44-9

betamethasone

21-Boc-glycyl-betamethasone

Conditions
ConditionsYield
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%
378-44-9

betamethasone

9α-fluoro-11β-hydroxy-16β-methylandrosta-1,4-diene-3,17-dione

Conditions
ConditionsYield
With bithmuth(III) triflate hydrate In 1,4-dioxane at 80℃; chemoselective reaction;68%
378-44-9

betamethasone

2921-14-4, 7776-18-3, 20295-82-3

(aminooxy)acetic acid hemihydrochloride

61600-49-5, 88378-32-9

betamethasome-3-(O-carboxymethy)oxime

Conditions
ConditionsYield
With pyridine In ethanol for 8h; Ambient temperature;55%
378-44-9

betamethasone

95-92-1

oxalic acid diethyl ester

C26H31FO7

Conditions
ConditionsYield
With sodium hydride In benzene for 24h; Cyclocondensation;50%
106-31-0

butanoic acid anhydride

378-44-9

betamethasone

betamethasone 21-butyrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; trichloroacetic acid In dichloromethane at 20℃;49%
4530-18-1

2-(tert-butoxycarbonylamino)-3-phenylpropionic acid

378-44-9

betamethasone

C36H46FNO8

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;18%
551-16-6

6-Aminopenicillanic Acid

378-44-9

betamethasone

541-41-3

chloroformic acid ethyl ester

19763-57-6, 19774-84-6

6β-(9-fluoro-11β,17-dihydroxy-16β-methyl-3,20-dioxo-pregna-1,4-dien-21-yloxycarbonylamino)-penicillanic acid

Conditions
ConditionsYield
(i) Et3N, THF, (ii) /BRN= 15080/, aq. KHCO3; Multistep reaction;
24823-81-2

trimethoxypropane

378-44-9

betamethasone

5534-13-4

Betamethasone propionate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;
43083-12-1

1,1,1-trimethoxybutane

378-44-9

betamethasone

5534-14-5

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17-butyrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;
13820-09-2

trimethyl orthovalerate

378-44-9

betamethasone

2152-44-5

betamethasone-valerate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;
51076-95-0

2-chloro-1,1,1-triethoxyethane

378-44-9

betamethasone

C26H34ClFO6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Ambient temperature;
58995-66-7

triethyl 2-methoxyorthoacetate

378-44-9

betamethasone

C27H37FO7

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Ambient temperature;
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2152-44-5
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Specification

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.