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378-44-9 Usage

hormone drugs

Betamethasone, belongs to adrenal corticosteroids, it is a isomer of dexamethasone , and the role of betamethasone is similiar to prednisolone and dexamethasone , it has anti-inflammatory, anti-rheumatic, anti-allergic and suppression of the immune and other pharmacological effects, its anti-inflammatory effect is stronger than dexamethasone, triamcinolone, hydrocortisone etc. , it can reduce and prevent tissue response to inflammation and eliminate heat, redness and swelling caused by local non-infectious inflammation, thereby reducing the performance of inflammation, anti-inflammatory effect of this product 0.3mg is equal to dexamethasone 0.75mg, prednisone 5mg or 25mg cortisone . Betamethasone sodium retention effect is a hundred times more than hydrocortisone, in primary adrenal hypofunction, it can be used together with glucocorticoid for replacement therapy ,and it is used for preventing or inhibiting cell-mediated immune response, delaying allergic reactions and reducing the primary immune response expansion ,it is used for low renin and low aldosterone syndrome and autonomic neuropathy induced orthostatic hypotension. Currently betamethasone is also used for the treatment of active rheumatoid arthritis, rheumatoid arthritis, lupus, severe bronchial asthma, severe dermatitis, acute leukemia, atopic dermatitis, eczema, neurodermatitis, seborrheic dermatitis, and pruritus and comprehensive treatment of certain infections. The product is contraindicated in severe psychiatric history, active duodenal ulcer, recent gastrointestinal anastomosis, heavier osteoporosis, overt diabetes, severe hypertension, virus , bacterial, fungal infections which are failed to control by the use of antimicrobial agents , thrombophlebitis, skin infections, such as impetigo, tinea, jock itch and so on. The above information is edited by the lookchem of Tian Ye.

Chemical Properties

Different sources of media describe the Chemical Properties of 378-44-9 differently. You can refer to the following data:
1. White crystalline powder. Mp 231-234 deg.] C (decomposition). Odorless. Acetate Betamethasone ([987-24-6]) is also white crystalline powder, melting point 205-208 ℃, slightly soluble in alcohol, ethanol, and very slightly soluble in chloroform or ether, insoluble in water, odorless.
2. White to Off-White Solid

Uses

Different sources of media describe the Uses of 378-44-9 differently. You can refer to the following data:
1. Hormone drugs.It is mainly used for anti-inflammatory and anti-allergic. It is suitable for rheumatoid arthritis and various skin diseases. Betamethasone role is similiar to dexamethasone, its anti-inflammatory effect is stronger than dexamethasone, triamcinolone, hydrocortisone and it has few side effects.
2. glucocorticoid, antiinflammatory
3. Betamethasone is a glucocorticoid used as an anti-inflammatory agent.
4. anti-inflammatory, immunosuppressive

production method

According to U.S. Patent No. 3,164,618, betamethasone acetate is dealt with hydrochloric acid in methanol-chloroform-water mixture , it can be converted to betamethasone.

Category

Toxic substances

Toxicity grading

Middle toxic

Acute toxicity

Oral-mouse LD50:> 4500 mg/kg

Flammability and hazard characteristics

Combustible;Its combustion produces toxic fumes of fluoride.

Storage Characteristics

Ventilated, low-temperature ,dry storeroom.

Extinguishing agent

Dry powder , foam, sand, carbon dioxide, water spray.

Description

Different sources of media describe the Description of 378-44-9 differently. You can refer to the following data:
1. Shortly after the introduction of dexamethasone, betamethasone, which differs from dexamethasone only in configuration of the 16-methyl group, was made available for the treatment of rheumatic diseases and dermatologic disorders. This analogue, which contains a 16β-methyl group, has received sufficient clinical trial examination to indicate that it is as effective as dexamethasone or, perhaps, even slightly more active. Although this drug has been reported to be less toxic than other steroids, some clinical investigators suggest that it is best used for short-term therapy.
2. Betamethasone is a synthetic corticosteroid. Like other corticosteroids, betamethasone has anti-inflammatory actions. Betamethasone also accelerates fetal lung maturation and has been used to decrease neonatal mortality and morbidity in infants born before 34 weeks of gestation.

Originator

Celestone,Schering,US,1961

Manufacturing Process

Betamethasone acetate is converted to betamethasone by means of hydrochloric acid in a methanol-chloroform-water mixture as described in US Patent 3,164,618.

Brand name

Celestone Syrup and Tablets (Schering).

Therapeutic Function

Glucocorticoid

General Description

Betamethasone, 9-fluoro-11β,17,21-trihydroxy-16β-methylpregna-1,4-diene-3,20-dione,is available as a variety of ester derivatives.Betamethasone valerate, USP (17-valerate)Betamethasone acetate, USP (21-acetate)Betamethasone sodium phosphate, USP (21-sodiumphosphate)Betamethasone dipropionate, USP (17-propionate,21-propionate).

Flammability and Explosibility

Nonflammable

Biochem/physiol Actions

Betamethasone, an?isomer?of dexamethasone is also termed as 9α-fluoro-16β-methyl-11 β,17,21-trihydroxypregna-1,4-dien-3,20-dione or 9α-fluoro-16β-methylprednisolone (27.1.52). It can be used as an anti-itch agent and treating dermatitis?and?eczema.

Clinical Use

Corticosteroid: Suppression of inflammatory and allergic disorders Congenital adrenal hyperplasia

Side effects

Toxic side effects, such as increased appetite, weight gain, and facial mooning, occur with prolonged use.

Safety Profile

Low toxicity by ingestion. Anexperimental teratogen. Other experimental reproductiveeffects. When heated to decomposition it emits toxicfumes of F-.

Synthesis

Betamethasone is 9α-fluoro-16β-methyl-11 β,17,21-trihydroxypregna- 1,4-dien-3,20-dione, or simply 9α-fluoro-16β-methylprednisolone (27.1.52). As seen from the chemical name of the drug, betamethasone only differs from dexamethasone in the orientation of the methyl group at C16. The proposed method of synthesis differs from the other method in a number of details and successive reactions besides the first stage, in particular concerning the addition of the methyl group at C16 of the steroid ring. Betamethasone, like dexamethasone, is synthesized from 3α-acetoxy-16-pregnen-11,20-dione; however, the methyl group at C16 of the steroid ring is not reacted with methylbromide, but rather is reacted with diazomethane followed by hydrogenation of the double bond between carbon atoms C16–C17 of the steroid ring using a palladium on carbon catalyst, which results in the corresponding β-orientation of the introduced methyl group.

Drug interactions

Potentially hazardous interactions with other drugs Aldesleukin: avoid concomitant use. Antibacterials: metabolism accelerated by rifampicin; metabolism possibly inhibited by erythromycin; concentration of isoniazid possibly reduced. Anticoagulants: efficacy of coumarins and phenindione may be altered. Antiepileptics: metabolism accelerated by carbamazepine, fosphenytoin, phenobarbital, phenytoin and primidone. Antifungals: increased risk of hypokalaemia with amphotericin - avoid; metabolism possibly inhibited by itraconazole and ketoconazole. Antivirals: concentration possibly increased by ritonavir. Ciclosporin: rare reports of convulsions in patients on ciclosporin and high-dose corticosteroids. Cobicistat: concentration of betamethasone possibly increased. Diuretics: enhanced hypokalaemic effects of acetazolamide, loop diuretics and thiazide diuretics. Vaccines: high dose corticosteroids can impair immune response to vaccines; avoid with live vaccines.

Metabolism

Corticosteroids are metabolised mainly in the liver but also in other tissues, and are excreted in the urine. The slower metabolism of the synthetic corticosteroids with their lower protein-binding affinity may account for their increased potency compared with the natural corticosteroids.

Purification Methods

Betamethasone crystallises from ethyl acetate, and has max at 238nm (log 4.18) in MeOH. The 21-acetate [287-24-6] crystallises from Me2CO/Et2O (charcoal) m 196-201o (205-208o) and has [] D 20 +140o (CHCl3). [Taub et al. J Am Chem Soc 82 4012 1960, Olivetto et al. J Am Chem Soc 80 6688 1958, Beilstein 8 IV 3501.]

references

[1] pharmacology review(s)-fda.

Check Digit Verification of cas no

The CAS Registry Mumber 378-44-9 includes 6 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 3 digits, 3,7 and 8 respectively; the second part has 2 digits, 4 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 378-44:
(5*3)+(4*7)+(3*8)+(2*4)+(1*4)=79
79 % 10 = 9
So 378-44-9 is a valid CAS Registry Number.
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;

378-44-9Relevant articles and documents

A variation of Mattox rearrangement mechanism under alkaline condition

Li, Min,Chen, Bin,Lin, Mingxiang,Chan, Tze-Ming,Fu, Xiaoyong,Rustum, Abu

, p. 3901 - 3905 (2007)

A variation of the Mattox rearrangement, a key degradation pathway under acidic conditions for corticosteroids possessing the 1,3-dihydroxyacetone side chain, has been found to occur for the 17,21-diesters of these corticosteroids but under the alkaline condition. The mechanism of this variation of the original Mattox rearrangement is proposed.

A 17, 21 - double-hydroxy steroid derivatives of synthetic method

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, (2018/04/02)

The invention relates to a method of preparing 17, 21-double-hydroxyl steroid derivatives by using 6, 9-substituted silyl steroid enol ether compound I as an initiator.

Ring opening and fluoridation method and device of steroidal epoxy compound

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Paragraph 0038; 0039; 0041, (2017/07/22)

The invention discloses a method of preparing a compound II, which is as shown as the following reaction formula as shown in the specification. A 9 alpha-fluorine-11 beta -hydroxyl steroidal compound II is prepared via epoxy compound ring opening and fluoridation of a steroidal epoxy compound I by taking hydrogen fluoride as a fluorination reagent in a solvent consisting of arene and water. In the formula, R is CH3, CH2OH or CH2OAc; R1 is OH; R2 is alpha-CH3 or beta-CH3; and R3 is F or H. A continuous reaction device as shown in Figure 1 can be used in the method.

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