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378-44-9 Usage

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

378-44-9 Well-known Company Product Price

Brand (Code)Product description CAS number Packaging Price Detail
TCI America (B1837)  Betamethasone  >98.0%(HPLC) 378-44-9 1g 410.00CNY Detail
TCI America (B1837)  Betamethasone  >98.0%(HPLC) 378-44-9 5g 1,230.00CNY Detail
Sigma-Aldrich (B1000000)  Betamethasone  European Pharmacopoeia (EP) Reference Standard 378-44-9 B1000000 1,880.19CNY Detail
USP (1066009)  Betamethasone  United States Pharmacopeia (USP) Reference Standard 378-44-9 1066009-200MG 4,662.45CNY Detail

378-44-9SDS

SAFETY DATA SHEETS

According to Globally Harmonized System of Classification and Labelling of Chemicals (GHS) - Sixth revised edition

Version: 1.0

Creation Date: Aug 11, 2017

Revision Date: Aug 11, 2017

1.Identification

1.1 GHS Product identifier

Product name betamethasone

1.2 Other means of identification

Product number -
Other names Bifas

1.3 Recommended use of the chemical and restrictions on use

Identified uses For industry use only.
Uses advised against no data available

1.4 Supplier's details

1.5 Emergency phone number

Emergency phone number -
Service hours Monday to Friday, 9am-5pm (Standard time zone: UTC/GMT +8 hours).

More Details:378-44-9 SDS

378-44-9Synthetic route

betamethasone 21-acetate
987-24-6

betamethasone 21-acetate

betamethasone
378-44-9

betamethasone

Conditions
ConditionsYield
With methanol; sodium methylate at 25℃; for 4h;90%
17α,21-dihydroxy-9β,11β-epoxy-16β-methylpregna-1,4-diene-3,20-dione
981-34-0

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

betamethasone
378-44-9

betamethasone

Conditions
ConditionsYield
With hydrogen fluoride In water; N,N-dimethyl-formamide at -15℃;89%
With hydrogen fluoride
C24H31FO5

C24H31FO5

betamethasone
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%
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

6β-hydroxybetamethasone
24703-00-2

6β-hydroxybetamethasone

D

6β-hydroxybetamethasone 17-propionate
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

betamethasone
378-44-9

betamethasone

Conditions
ConditionsYield
With sodium methylate
betamethasone dipropionate
5593-20-4

betamethasone dipropionate

A

betamethasone
378-44-9

betamethasone

B

Betamethasone propionate
5534-13-4

Betamethasone propionate

C

betamethasone 21-monopropionate

betamethasone 21-monopropionate

Conditions
ConditionsYield
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
884488-47-5

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

betamethasone
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
16β-methyl-9β,11β-epoxy-17α-hydroxy-1,4-pregnadiene-3,20-dione
37413-99-3

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

betamethasone
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
16β-methyl-3β,17α-dihydroxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
884488-49-7

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

betamethasone
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
3β-acetoxy-16α,17α-epoxy-20,20-ethylenedioxy-5α-pregn-9(11)-ene
884488-48-6

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

betamethasone
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
(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
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

betamethasone
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
16β-methyl-17α-hydroxy-pregna-1,4,9(11)-triene-3,20-dione
14135-32-1

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

betamethasone
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
20-oxo-5α-pregna-9(11),16-dien-3β-yl acetate
21650-83-9

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

betamethasone
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
Δ9(11)22-isoallospirosten-3β-ol
1106-20-3

Δ9(11)22-isoallospirosten-3β-ol

betamethasone
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
3β-acetoxy-16α,17α-epoxy-5α-pregn-9(11)-en-20-one
113926-56-0

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

betamethasone
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
Δ9(11)22-isoallospirosten-3β-ol-12-one-3-acetate
989-73-1

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

betamethasone
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
16β-methyl-9α-fluoro-11β,17α-dihydroxy-1,4-pregnadiene-3,20-dione
1879-77-2

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

betamethasone
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
hecogenin
467-55-0

hecogenin

betamethasone
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
hecogenin acetate
915-35-5

hecogenin acetate

betamethasone
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

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

betamethasone
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

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

betamethasone
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

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

betamethasone
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

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

betamethasone
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
21-acetyloxy-17α-hydroxy-16β-methylpregna-4,9(11)-diene-3,20-dione
18762-17-9

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

betamethasone
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

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

betamethasone
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
androst-4,9(11)-dien-3,17-dione
1035-69-4

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

betamethasone
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

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

betamethasone
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

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

betamethasone
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

C24H29FO5

betamethasone
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
3-(tert-butyloxycarbonylamino)propionic acid
3303-84-2

3-(tert-butyloxycarbonylamino)propionic acid

betamethasone
378-44-9

betamethasone

Boc-β-alanine-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

C8H14ClNO4

betamethasone
378-44-9

betamethasone

C30H41ClFNO8

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

Fmoc-Orn(Boc)-OH

betamethasone
378-44-9

betamethasone

C47H57FN2O10

C47H57FN2O10

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 20℃; Cooling with ice;99%
3-[(tert-butoxycarbonyl)amino]-2-fluoropropanoic acid

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

betamethasone
378-44-9

betamethasone

C30H41F2NO8

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%
L-N-Boc-Ala
15761-38-3

L-N-Boc-Ala

betamethasone
378-44-9

betamethasone

21-Boc-alanyl-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%
betamethasone
378-44-9

betamethasone

9α-fluoro-11β,17α-dihydroxy-16β-methyl-3-oxo-androsta-1,4-diene-17β-carboxylic acid
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
betamethasone
378-44-9

betamethasone

Triethyl orthoacetate
78-39-7

Triethyl orthoacetate

betamethasone 17-acetate
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%
betamethasone
378-44-9

betamethasone

clobetasol

clobetasol

Conditions
ConditionsYield
With pyridine; dichlorohydantoin; sulfur dioxide In N,N-dimethyl-formamide at 5℃; for 2h;95.6%
C8H14BrNO4

C8H14BrNO4

betamethasone
378-44-9

betamethasone

C30H41BrFNO8

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%
N-Methylhydroxylamine
593-77-1

N-Methylhydroxylamine

betamethasone
378-44-9

betamethasone

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-3-methylimino-1,4-pregnadien-20-one N-oxide
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%
N-(t-butoxycarbonyl)-isoleucine
13139-16-7

N-(t-butoxycarbonyl)-isoleucine

betamethasone
378-44-9

betamethasone

C33H48FNO8

C33H48FNO8

Conditions
ConditionsYield
With dmap In dichloromethane; N,N-dimethyl-formamide at 0 - 20℃;87%
N-(tert-butyloxycarbonyl)-L-isoleucine
13139-16-7

N-(tert-butyloxycarbonyl)-L-isoleucine

betamethasone
378-44-9

betamethasone

21-(Boc-isoleucyl)-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%
betamethasone
378-44-9

betamethasone

1-(13-cis-Retinoyl)imidazole
85610-79-3

1-(13-cis-Retinoyl)imidazole

C43H53FO7

C43H53FO7

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

formaldehyd

betamethasone
378-44-9

betamethasone

C24H31FO6

C24H31FO6

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

BOC-glycine

betamethasone
378-44-9

betamethasone

21-Boc-glycyl-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%
betamethasone
378-44-9

betamethasone

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

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%
betamethasone
378-44-9

betamethasone

(aminooxy)acetic acid hemihydrochloride
2921-14-4, 7776-18-3, 20295-82-3

(aminooxy)acetic acid hemihydrochloride

betamethasome-3-(O-carboxymethy)oxime
61600-49-5, 88378-32-9

betamethasome-3-(O-carboxymethy)oxime

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

betamethasone

oxalic acid diethyl ester
95-92-1

oxalic acid diethyl ester

C26H31FO7

C26H31FO7

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

butanoic acid anhydride

betamethasone
378-44-9

betamethasone

betamethasone 21-butyrate

betamethasone 21-butyrate

Conditions
ConditionsYield
With toluene-4-sulfonic acid; trichloroacetic acid In dichloromethane at 20℃;49%
2-(tert-butoxycarbonylamino)-3-phenylpropionic acid
4530-18-1

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

betamethasone
378-44-9

betamethasone

C36H46FNO8

C36H46FNO8

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

6-Aminopenicillanic Acid

betamethasone
378-44-9

betamethasone

chloroformic acid ethyl ester
541-41-3

chloroformic acid ethyl ester

6β-(9-fluoro-11β,17-dihydroxy-16β-methyl-3,20-dioxo-pregna-1,4-dien-21-yloxycarbonylamino)-penicillanic acid
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;
trimethoxypropane
24823-81-2

trimethoxypropane

betamethasone
378-44-9

betamethasone

Betamethasone propionate
5534-13-4

Betamethasone propionate

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

1,1,1-trimethoxybutane

betamethasone
378-44-9

betamethasone

9α-fluoro-11β,17α,21-trihydroxy-16β-methyl-1,4-pregnadiene-3,20-dione 17-butyrate
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;
trimethyl orthovalerate
13820-09-2

trimethyl orthovalerate

betamethasone
378-44-9

betamethasone

betamethasone-valerate
2152-44-5

betamethasone-valerate

Conditions
ConditionsYield
With toluene-4-sulfonic acid In N,N-dimethyl-formamide; benzene for 1.25h; Ambient temperature;
2-chloro-1,1,1-triethoxyethane
51076-95-0

2-chloro-1,1,1-triethoxyethane

betamethasone
378-44-9

betamethasone

C26H34ClFO6

C26H34ClFO6

Conditions
ConditionsYield
With toluene-4-sulfonic acid In tetrahydrofuran for 12h; Ambient temperature;
triethyl 2-methoxyorthoacetate
58995-66-7

triethyl 2-methoxyorthoacetate

betamethasone
378-44-9

betamethasone

C27H37FO7

C27H37FO7

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

378-44-9Upstream product

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