50-04-4

Basic information

• Product Name: Cortisone acetate
• Synonyms: 11,20-trione,17,21-dihydroxy-pregn-4-ene-21-acetate;11-dehydro-17-hydroxycorticosterone-21-acetate;11-dehydro-17-hydroxycorticosteroneacetate;17,21-dihydroxypregn-4-ene-3,11,20-trioneacetate;20-trione,21-(acetyloxy)-17-hydroxy-pregn-4-ene-11;21-(acetyloxy)-17-hydroxypregn-4-ene-3,11,20-trione;21-acetoxy-17,alpha-hydroxy-3,11,20-triketopregnene-4;21-acetoxy-17,alpha-hydroxypregn-4-ene-3,11,20-trione
• CAS NO: 50-04-4
• Molecular Formula: C₂₃H₃₀O₆
• Molecular Weight: 402.48
• EINECS: 200-006-5
• Product Categories: Biochemistry;Hydroxyketosteroids;Steroids;CORTONE;Hormone Drugs;Inhibitors
• Mol File: 50-04-4.mol

Chemical Properties

• Melting Point: 237-240 °C(lit.)
• Boiling Point: 567.8 °C at 760 mmHg
• Flash Point: 311.2 °C
• Appearance: solid
• Density: 1.28 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 212 ° (C=1, MeOH)
• Storage Temp.: 2-8°C
• Solubility: Practically insoluble in water, freely soluble in methylene chloride, soluble in dioxan, sparingly soluble in acetone, slightly soluble in ethanol (96 per cent) and in methanol.
• PKA: 12.32±0.60(Predicted)
• Water Solubility: 19mg/L(25 oC)
• Stability: Stable. Incompatible with strong oxidizing agents.
• Merck: 14,2539
• BRN: 2067543
• CAS DataBase Reference: Cortisone acetate(CAS DataBase Reference)
• NIST Chemistry Reference: Cortisone acetate(50-04-4)
• EPA Substance Registry System: Cortisone acetate(50-04-4)

Safety Data

• Safety Statements: 22-36/37-24/25
• WGK Germany: 3
• RTECS: GM9140000
• Hazardous Substances Data: 50-04-4(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
Cortisone acetate is used as an anti-inflammatory agent for treating various conditions such as collagen diseases, Addison's disease, severe shock, allergic conditions, chronic lymphocytic leukemia, and many other indications. It is bioavailable and readily converted to the therapeutically active form, hydrocortisone.
Used in Dermatological Applications:
Cortisone acetate is used as a topical medication for relieving inflammation and pruritic manifestations of corticosteroid-responsive dermatoses. It is also used in the treatment of immune and allergic disorders.
Used in Veterinary Medicine:
Cortisone acetate is used in rabbits to decrease the size of Bacillus Calmette-Guérin (BCG) vaccine-induced dermal lesions and tuberculin reactions when administered at 2 mg/kg on alternate days over the course of 46 days. It also reduces the number and percentage of activated lesion-infiltrating mononuclear cells and decreases the amount of caseous necrosis and ulceration. Additionally, cortisone acetate (2.5 mg/kg per day, s.c.) slows tissue regeneration in a rabbit model of wound healing.
Used in Research:
Cortisone acetate is used to study its effects on the number of dexamethasone binding sites on isolated human lymphocytes, as it has been shown to decrease these sites by 30%.

Originator

Cortone Acetate,MSD,US,1950

Manufacturing Process

The following technique is described in US Patent 2,541,104. A solution of 2.0 g of 3(α)-hydroxy-21-acetoxy-11,20-diketo-pregnane, which can be prepared as described in Helv. Chim. Acta 27, 1287 (1944), is treated in a mixture of 25 cc of alcohol and 6.4 cc of acetic acid at 0°C with 6.0 g of potassiumcyanide. The solution is allowed to warm to room temperature and after 3 hours is diluted with water. The addition of a large volume of water to the alcohol-hydrogen cyanide mixture precipitates a gum which is extracted with chloroform or ethyl acetate. The extract is washed with water, and evaporated to small volume under reduced pressure. The crystalline precipitate (1.3 g) consists of 3(α),20-dihydroxy-20-cyano-21-acetoxy-11-keto-pregnane; dec. 175° to 185°C.A solution of 0.60 g of chromic acid in 1.2 cc of water and 11 cc of acetic acid is added to a solution containing about 1.2 g of 3(α),20-dihydroxy-20-cyano- 21-acetoxy-11-ketopregnane at room temperature. After 1 hour, water is added and the product, which precipitates, is filtered and recrystallized from ethyl acetate to produce 3,11-diketo-20-hydroxy-20-cyano-21-acetoxypregnane; dec. 214° to 217°C. 0.40 cc of phosphorus oxychloride is added to a solution containing about 950 mg of 3,11-diketo-20-hydroxy-20-cyano-21-acetoxy-pregnane dissolved in 3 cc of pyridine. After standing at room temperature for 24 hours, the solution is poured into water and dilute hydrochloric acid, extracted with benzene and concentrated to dryness. The crude product, after chromatography gives one main constituent, namely δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene; MP 189° to 190°C. A solution of 1.0 g of δ17-3,11-diketo-20-cyano-21-acetoxy-pregnene in 10 cc of benzene is treated with 1.0 g of osmium tetroxide and 0.43 g of pyridine. After standing at room temperature for 18 hours, the resulting solution is treated successively with 50 cc of alcohol, and with 50 cc of water containing 2.5 g of sodium sulfite. The mixture is stirred for 30 hours, filtered, and the filtrate acidified with 0.5 cc of acetic acid and concentrated to small volume in vacuo. The aqueous suspension is then extracted four times with chloroform, the chloroform extracts are combined, washed with water and concentrated to dryness in vacuo. Recrystallization of the residue from acetone gives 9°C. This compound is then treated with acetic anhydride and pyridine for 15 minutes at room temperature to produce 3,11,20-triketo-17(α)-hydroxy-21-acetoxypregnane or cortisone acetate.

Therapeutic Function

Glucocorticoid

Purification Methods

Crystallise -1cortisone-21-acetate from acetone or CHCl3. The UV has 15,800 M-1cm at 238nm in dioxane. [Sarett J Biol Chem 162 601 1946, Beilstein 8 III 4058, 5 IV 3481.]

InChI:InChI=1/C23H30O6/c1-13(24)29-12-19(27)23(28)9-7-17-16-5-4-14-10-15(25)6-8-21(14,2)20(16)18(26)11-22(17,23)3/h10,16-17,20,28H,4-9,11-12H2,1-3H3/t16-,17-,20+,21+,22+,23+/m1/s1

Synthetic route

anecortave (7753-60-8) → Cortisone acetate (50-04-4)

Conditions	Yield
Stage #1: anecortave With tetrafluoroboric acid In dichloromethane; acetone at -5 - 0℃; for 5h; Inert atmosphere; Stage #2: With Jones reagent In dichloromethane; acetone at 0 - 5℃; for 4h; Reagent/catalyst; Solvent; Temperature; Inert atmosphere;	95.8%

Acetic acid 2-hydroxy-2-((8S,9S,10R,13S,14S,17R)-17-hydroxy-10,13-dimethyl-3,11-dioxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-ethyl ester → Cortisone acetate (50-04-4)

Conditions	Yield
With 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione In dimethyl sulfoxide at 50℃; for 3h;	93%

hydrocortisone acetate → Cortisone acetate (50-04-4)

Conditions	Yield
With [2,2]bipyridinyl; trimethylsilyl trifluoromethanesulfonate; bis(acetoxy)iodylbenzene In dichloromethane at 20℃; for 0.5h;	93%

21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione (50733-54-5) → Cortisone acetate (50-04-4)

Conditions	Yield
With di-tert-butyl peroxide In tetrahydrofuran Inert atmosphere; Reflux;	90%

C23H29BrO6 → Cortisone acetate (50-04-4)

Conditions	Yield
With acetic acid; zinc In dichloromethane at 10℃; for 3h; Temperature;	79.5%

hydrocortisone acetate (50-03-3) → Cortisone acetate (50-04-4)

Conditions	Yield
With chromium(VI) oxide; acetic acid
With pyridine; magnesium sulfate; pyridinium chlorochromate at 0 - 25℃; for 12h;
With chromium(VI) oxide; acetic acid; manganese(ll) chloride In chloroform; water at 30℃; Solvent; Reagent/catalyst; Temperature;	19.2 g

21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione (1499-59-8) → Cortisone acetate (50-04-4)

Conditions	Yield
With bromine durch aufeinanderfolgende Umsetzung mit Semicarbazid und mit Brenztraubensaeure;

21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione (988-16-9) → Cortisone acetate (50-04-4)

Conditions	Yield
With toluene-4-sulfonic acid

hydrocortisone acetate (50-03-3) → (8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-dimethyl-1,6,7,8,9,10,11,12,13,14,15,16-dodecahydro-2H-cyclopenta[a]phenanthrene-3,17-dione (382-44-5) + Cortisone acetate (50-04-4)

Conditions	Yield
Product distribution; Rate constant; Irradiation; radiolytic degradation;

21-acetoxy-11α,17-dihydroxy-pregn-4-ene-3,20-dione → Cortisone acetate (50-04-4)

Conditions	Yield
With chromium(VI) oxide

21-acetoxy-pregna-4,17(2O)c-diene-3,11-dione → Cortisone acetate (50-04-4)

Conditions	Yield
With osmium(VIII) oxide; triethylamine N-oxide; dihydrogen peroxide

hydrocortisone acetate (50-03-3) + acetic acid (64-19-7) + CrO3 → Cortisone acetate (50-04-4)

21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione (111615-16-8) + acetic acid (64-19-7) + CrO3 → Cortisone acetate (50-04-4) + adrenosterone (382-45-6)

HYDROCORTISONE (50-23-7) → Cortisone acetate (50-04-4)

Conditions	Yield
Multi-step reaction with 2 steps 1: pyridine 2: CrO3; acetic acid View Scheme

11α-hydroxy-16α,17α-epoxyprogesterone (3684-83-1, 19427-36-2, 95975-59-0) → Cortisone acetate (50-04-4)

Conditions	Yield
Multi-step reaction with 5 steps 1: hydrogen bromide / 5 h / 5 - 10 °C 2: hydrogen; acetic acid / ethanol / 3 h / 40 - 45 °C 3: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C 4: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C 5: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C View Scheme

11α,17α-dihydroxy-16β-bromo progesterone → Cortisone acetate (50-04-4)

Conditions	Yield
Multi-step reaction with 4 steps 1: hydrogen; acetic acid / ethanol / 3 h / 40 - 45 °C 2: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C 3: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C 4: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C View Scheme

11α,17α-dihydroxypregn-4-ene-3,20-dione (603-98-5) → Cortisone acetate (50-04-4)

Conditions	Yield
Multi-step reaction with 3 steps 1: bromine; hydrogenchloride / ethanol; chloroform / 1 h / 20 - 25 °C 2: N,N-dimethyl-formamide / 0.5 h / 35 - 40 °C 3: manganese(ll) chloride; acetic anhydride; acetic acid / water / 4 h / 5 - 10 °C View Scheme

11α,17α-dihydroxyprogesterone-21-acetate (1250-97-1) → Cortisone acetate (50-04-4)

Conditions	Yield
With acetic anhydride; acetic acid; manganese(ll) chloride In water at 5 - 10℃; for 4h;	29.1 g

21-acetoxy-9-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione (2206-03-3) → Cortisone acetate (50-04-4)

Conditions	Yield
With acetic acid; zinc In chloroform at 10 - 15℃; for 10h; Solvent; Inert atmosphere;	32.6 g

17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate (1249-67-8) → cortexolone 21-acetate (640-87-9) + Cortisone acetate (50-04-4)

Conditions	Yield
Stage #1: 17α,21-dihydroxypregna-1,4-diene-3,20-dione 21-acetate With potassium carbonate; sodium hydroxide In methanol; chloroform at -5 - 5℃; for 0.333333h; Inert atmosphere; Stage #2: With acetic acid In methanol; chloroform Inert atmosphere; Stage #3: With methanol; acetic anhydride; triethylamine In dichloromethane Reagent/catalyst; Solvent; Temperature;

Cortisone acetate (50-04-4) → adrenosterone (382-45-6)

Conditions	Yield
Stage #1: Cortisone acetate With sodium tetrahydroborate In ethanol; dichloromethane for 1.5h; Inert atmosphere; Stage #2: With sodium periodate In water; acetone at 20℃; for 0.75h; Inert atmosphere;	86%
Product distribution; Rate constant; Irradiation; radiolytic degradation;

Cortisone acetate (50-04-4) → 21-acetoxy-17α-hydroxypregna-3,5-diene-11,20-dione

Conditions	Yield
Stage #1: Cortisone acetate With C19H26ClIrN3O(1+)*Cl(1-) In water; acetonitrile at 80℃; for 0.166667h; Green chemistry; Stage #2: With formic acid In water; acetonitrile at 80℃; for 8h; Green chemistry; regioselective reaction;	81%

Cortisone acetate (50-04-4) + trimethyl orthoformate (149-73-5) → (2R,3aR,3bS,5aS,6R,8aS,8bS)-6-(2-Acetoxy-acetyl)-6-hydroxy-3a,5a-dimethyl-4-oxo-2,3,3a,3b,4,5,5a,6,7,8,8a,8b,9,10-tetradecahydro-dicyclopenta[a,f]naphthalene-2-carboxylic acid methyl ester

Conditions	Yield
With thallium(III) nitrate In methanol at 0℃; for 0.5h;	66%

Cortisone acetate (50-04-4) → Cortisone (53-06-5)

Conditions	Yield
With lipase from Candida cylindracea; octanol In water; acetonitrile at 37℃; for 144h;	62%
With potassium hydrogencarbonate
With potassium hydroxide
With sodium methylate

formaldehyd (50-00-0) + Cortisone acetate (50-04-4) → 17α,20;20,21-bismethylenedioxypregn-4-ene-3,11-dione (3607-68-9)

Conditions	Yield
With hydrogenchloride In chloroform; water at 23℃; for 12h; Inert atmosphere;	61%

Cortisone acetate (50-04-4) → 17α,21-dihydroxy-pregna-4,6-diene-3,11,20-trione 21-acetate (2435-02-1)

Conditions	Yield
With chloranil In tert-butyl alcohol for 7h; Heating;	60%
With chloranil; xylene
Multi-step reaction with 3 steps 1: N-bromo-succinimide 2: salicylic acid 3: 4-hydroxy-benzaldehyde View Scheme

diazomethane (186581-53-3, 908094-01-9) + Cortisone acetate (50-04-4) → 20,21-epoxy-17,22-dihydroxy-23,24-dinor-20ξH-chol-4-ene-3,11-dione (115388-24-4)

Conditions	Yield
With methanol; diethyl ether

2-ethyl-2-methyl-1,3-dioxolane (126-39-6) + Cortisone acetate (50-04-4) → 21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione (988-16-9)

Conditions	Yield
With toluene-4-sulfonic acid

O-Methylhydroxylamin (67-62-9) + Cortisone acetate (50-04-4) → 21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-bis-(O-methyl oxime ) (125496-85-7)

2-methallyl-2-methyl-[1,3]dioxolane (4362-28-1) + Cortisone acetate (50-04-4) → 21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione (988-16-9)

Conditions	Yield
With tetrahydrofuran; sulfuric acid

Cortisone acetate (50-04-4) → prednisone acetate (125-10-0)

Conditions	Yield
With selenium(IV) oxide
With periodic acid
With iodine pentoxide
With Arthrobacter simplex By-2-13	17 g

Cortisone acetate (50-04-4) → 21-acetoxy-4-chloro-17-hydroxy-pregn-4-ene-3,11,20-trione (28444-83-9)

Conditions	Yield
With hypochloric acid
Multi-step reaction with 2 steps 1: diethyl ether; propionic acid; chlorine 2: pyridine View Scheme
Multi-step reaction with 2 steps 1: aqueous perchloric acid / Erwaermen des Reaktionsprodukts mit Kaliumacetat in Aceton und danach mit Acetanhydrid und Pyridin 2: HCl View Scheme

Cortisone acetate (50-04-4) → 21,21-dimethoxy-pregn-4-ene-3,11,20-trione (68599-17-7)

Conditions	Yield
With hydrogenchloride

Cortisone acetate (50-04-4) → 17-acetoxy-D-homo-androsta-4,16-diene-3,11,17a-trione + 17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione (102084-08-2)

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene beim anschliessender Acetylierung;

Cortisone acetate (50-04-4) → 17β-acetoxymethyl-17α-hydroxy-D-homo-androst-4-ene-3,11,17a-trione (102084-08-2)

Conditions	Yield
With cyclohexanone; aluminum isopropoxide; toluene
With cyclohexanone; aluminum isopropoxide In toluene

Cortisone acetate (50-04-4) → 21-acetoxy-6ξ-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione (426833-73-0)

Conditions	Yield
With N-Bromosuccinimide

Cortisone acetate (50-04-4) → 21-acetoxy-4β,5-dichloro-17-hydroxy-5α-pregnane-3,11,20-trione (113862-15-0)

Conditions	Yield
With diethyl ether; chlorine; propionic acid

Cortisone acetate (50-04-4) → 21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3-oxime (100437-38-5)

Conditions	Yield
With hydrogenchloride; hydroxylamine

Cortisone acetate (50-04-4) → 21-acetoxy-17-hydroxy-pregn-4-ene-3,11,20-trione-3,20-dioxime (124113-30-0)

Conditions	Yield
With hydrogenchloride; hydroxylamine

Cortisone acetate (50-04-4) → 21-acetoxy-17,20βF-dihydroxy-pregn-4-ene-3,11-dione (111615-16-8)

Conditions	Yield
With sodium tetrahydroborate

Cortisone acetate (50-04-4) → 21-acetoxy-17-hydroxy-5α-pregn-3-ene-11,20-dione (114178-95-9) + 21-acetoxy-17-hydroxy-5β-pregn-3-ene-11,20-dione (114178-96-0)

Conditions	Yield
With acetic acid; zinc

Cortisone acetate (50-04-4) → 21-acetoxy-17-hydroxy-5α-pregnane-3,11,20-trione (3751-02-8)

Conditions	Yield
With palladium Hydrogenation;

Cortisone acetate (50-04-4) → 4α,5α-epoxyandrostene-3,11,17-trione (17597-29-4) + 4ξ,5-epoxy-17α-hydroxy-3,11-dioxo-5ξ-androstane-17β-carboxylic acid (102454-93-3)

Conditions	Yield
With methanol; sodium hydroxide; dihydrogen peroxide

Cortisone acetate (50-04-4) → 21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione (988-16-9)

Conditions	Yield
With toluene-4-sulfonic acid; ethylene glycol; benzene
With toluene-4-sulfonic acid; ethylene glycol unter vermindertem Druck;

Upstream product

• 50-03-3 hydrocortisone acetate 
• 1499-59-8 21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione 
• 988-16-9 21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione 
• 50-23-7 HYDROCORTISONE 
• 3684-83-1 11α-hydroxy-16α,17α-epoxyprogesterone 
• 603-98-5 11α,17α-dihydroxypregn-4-ene-3,20-dione 
• 1250-97-1 11α,17α-dihydroxyprogesterone-21-acetate 
• 2206-03-3 21-acetoxy-9-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione 
• 7753-60-8 anecortave 
• 50733-54-5 21-acetoxy-9-bromo-11β,17-dihydroxy-pregn-4-ene-3,20-dione 
• 117900-52-4 rac-21-acetoxy-16β-bromo-17-hydroxy-pregn-4-ene-3,11,20-trione 
• 988-16-9 rac-21-acetoxy-3,3-ethanediyldioxy-17-hydroxy-pregn-5-ene-11,20-dione 
• 94686-89-2 rac-16α,17α-epoxy-3,11-dioxo-androst-4-ene-17β-carboxylic acid 
• 123267-87-8 rac-21-acetoxy-16α,17-epoxy-pregn-4-ene-3,11,20-trione 

Downstream Products

• 53-06-5 Cortisone 
• 125-10-0 prednisone acetate 
• 28444-83-9 4-Chlor-cortison-21-acetat 
• 3751-02-8 21-acetoxy-17-hydroxy-5α-pregnane-3,11,20-trione 
• 382-45-6 adrenosterone 
• 1418283-94-9 C₂₃H₃₂O₅ 
• 1499-59-8 21-acetoxy-17-hydroxy-5β-pregnane-3,11,20-trione 
• 17736-20-8 3α,17,21-trihydroxy-5β-pregnane-11,20-dione 21-acetate 
• 17520-02-4 3β-Hydroxy-androsten-(5)-dion-(11,17) 
• 13096-52-1 21-acetoxy-6β,17-dihydroxy-pregn-4-ene-3,11,20-trione 
• 16355-28-5 6β,17,21-trihydroxypregn-4-ene-3,11,20-trione 
• 53-03-2 Prednison 
• 50-23-7 HYDROCORTISONE 

Relevant articles and documents

Method for treating prednisone acetate mother liquor

The invention relates to the technical field of chemical pharmacy, in particular to a method for treating prednisone acetate mother liquor. The method comprises the following steps: (1) adding a solvent and alkali liquor into the prednisone acetate mother liquor to carry out hydrolysis reaction; (2) after the hydrolysis reaction is finished, adjusting the reaction liquid to be neutral, concentrating under reduced pressure until a large amount of crystals are separated out, and performing suction filtration to obtain a hydrolysate crude product; (3) adding the hydrolysate crude product into a solvent, and refining to obtain a hydrolyzed refined product; (4) adding the hydrolyzed refined substance and a catalyst into a solvent, and reacting with acetic anhydride to obtain a mixture of prednisone acetate and cortisone acetate; and (5) fermenting and dehydrogenating the mixture to obtain the prednisone acetate. According to the treatment method, the prednisone acetate in the prednisone acetate mother liquor can be recycled, particularly, the prednisone acetate in the mother liquor can be recycled, the treatment cost is saved, and the yield of the prednisone acetate is increased; The method can well remove the dehydrogenation RSA and RSA impurities, and is stable in processand simple to operate.

Bidentate Nitrogen-Ligated I(V) Reagents, Bi(N)-HVIs: Preparation, Stability, Structure, and Reactivity

Hypervalent iodine(V) reagents are a powerful class of organic oxidants. While the use of I(V) compounds Dess-Martin periodinane and IBX is widespread, this reagent class has long been plagued by issues of solubility and stability. Extensive effort has been made for derivatizing these scaffolds to modulate reactivity and physical properties but considerable room for innovation still exists. Herein, we describe the preparation, thermal stability, optimized geometries, and synthetic utility of an emerging class of I(V) reagents, Bi(N)-HVIs, possessing datively bound bidentate nitrogen ligands on the iodine center. Bi(N)-HVIs display favorable safety profiles, improved solubility, and comparable to superior oxidative reactivity relative to common I(V) reagents. The highly modular synthesis and in situ generation of Bi(N)-HVIs provides a novel and convenient screening platform for I(V) reagent and reaction development.

Preparation method of prednisone

The invention discloses a preparation method of prednisone, and belongs to the technical field of preparation and processing of medicines. According to the method, hydrocortisone acetate is used as aninitial raw material, and the prednisone is prepared through three steps of oxidation, biological fermentation dehydrogenation and hydrolysis. According to the preparation method of prednisone, the defects of a traditional process are overcome, the target product is high in purity, good in quality stability, high in yield, low in production cost and mild in reaction condition, a highly toxic cyanide reagent is prevented from being used, and the method is easy and convenient to operate, suitable for industrial production and wide in market prospect.

Dehalogenation methodof 9-halogenated steroid compound and application

The invention provides a dehalogenation method of a 9-halogenated steroid compound and application, and relates to the technical field of chemical synthesis. The dehalogenation method of the 9-halogenated steroid compound comprises the following steps: reacting a compound I with a hydrogen donor and an azo radical initiator to obtain a 9-dehalogenated product compound II of the 9-halogenated steroid compound. According to the dehalogenation method of the 9-halogenated steroid compound, a hydrogen donor adopts one or a combination of more of hypophosphorous acid and hypophosphite, formic acid and formate, organic silicon hydride, hydrazine compounds or cyclohexene, and an initiator adopts an azo free radical initiator. Reagents such as chromium, divalent chromium salt, trivalent chromium salt or tributyltin hydride which are high in toxicity and cause serious pollution to the environment are not used in the reaction, the method is green and environmentally friendly, the synthesis process is simple, convenient and easy to implement, and the production applicability is improved.

9-site dehalogenation preparation method of 9-halogenated steroid hormone compound

The invention discloses a 9-site dehalogenation method of a steroid hormone compound. The method comprises the following steps of: dissolving a 9-halogenated-11-hydroxy steroid compound or a 9-halogenated-11-hydroxy ester steroid compound into an organic solvent; heating to a certain temperature, slowly adding a proper amount of a dehalogenation reagent, carrying out a reaction for a period of time, carrying out detection, carrying out reduced pressure concentration to remove a part of the solvent after the reaction is completed, carrying out cooling crystallization or crystallization by adding water, separating out a solid, and filtering to obtain the target product that is a 11-carbonyl steroid compound or a 11-hydroxy ester steroid compound. The method has the advantages of simple operation, few reaction impurities, high yield, capability of avoiding of the use of a metal dehalogenation agent and mercaptofatty acid, reduction of three-waste pollution, and suitableness for industrialproduction.

Preparation method of cortisone-21-acetate

The invention provides a preparation method of cortisone-21-acetate. The preparation method comprises: A) in a protective atmosphere, mixing a compound as shown in a formula I with anhydrous dimethylsulfoxide, a halogenating reagent and a first acid catalyst to carry out an addition-elimination reaction, so as to obtain a compound as shown in a formula III; B) adding the compound shown in the formula III into an organic solvent, and then adding a second acid catalyst and a reducing agent for a reduction reaction to obtain cortisone-21-acetate. The reaction formula is shown in the description.According to the preparation method, a Jones reagent does not need to be adopted, generation of a large amount of chromium-containing wastewater is avoided, the production period is shortened, the production cost is reduced, and clean production is achieved. The purity of the cortisone-21-acetate prepared by the method reaches 99.0% or above, the yield reaches 93% or above, and the preparation method is simple to operate, energy-saving, consumption-reducing, environment-friendly, and particularly suitable for industrial production.

Method for preparing cortisone acetate in one pot

Provided is a method for preparing cortisone acetate in one pot. According to the method, Anecortave acetate is adopted as a raw material, and after the raw material is added into an organic solvent,a pot is adopted for preparation. The method comprises the following steps of A, adding a compound I into a mixed organic solvent and adding a halogenating reagent and an acid catalyst, wherein the reaction temperature is controlled in a range from -10 DEG C to 30 DEG C; after the reaction is finished, adding a quencher to quench the reaction, wherein the quencher comprises a sodium sulfite solution or a sodium bisulfite solution; B, adding an oxidant into a system finally obtained in step A, wherein the oxidant is a Jones reagent or pyridine chlorochromate or a Dess-Martin oxidant used for anoxidization reaction, and the reaction temperature is controlled in a range from -10 DEG C to 30 DEG C; after the reaction is finished, adding the quencher to quench the reaction; C, adding an organic acid catalyst and a reducing agent into an organic layer finally obtained in step B to obtain a target product cortisone acetate IV. The preparation method greatly reduces the discharge amount of waste liquid.

OXYSTEROLS AND METHODS OF USE THEREOF

Compounds are provided according to Formula (I): and pharmaceutically acceptable salts thereof, and pharmaceutical compositions thereof; wherein R1, R2, R3, and R6, R11a, and R11b are as defined herein. Compounds of the present invention are contemplated useful for the prevention and treatment of a variety of conditions.

Preparation method of cortisone acetate

The invention relates to a preparation method of cortisone acetate. Anecortave acetate is used as a raw material and sequentially takes addition, oxidization and reduction reaction to obtain the anecortave acetate. The method comprises the following reaction steps of A, addition reaction: under the nitrogen production, adding the anecortave acetate into an organic solvent; adding a halogenating reagent and an acid catalyst to obtain an intermediate II; B, oxidization reaction: under the nitrogen gas protection, adding the compound II into the organic solvent; adding an oxidizing agent to obtain an intermediate III; C, reduction reaction: under the nitrogen gas production, adding the compound III into the organic solvent; adding an acid catalyst and a reducing agent to obtain a target product of the cortisone acetate IV. The method has the advantages that the raw materials can be easily obtained; the reaction steps are few; the quality and the yield achieve the obvious competitiveness; in addition, the pollution on the environment is reduced.

A process for the preparation of hydrocortisone acetate

The invention discloses a preparation method of cortisone acetate, and belongs to the field of pharmaceutical chemistry. According to the method, 11 alpha-hydroxy- 16 alpha, 17 alpha-epoxy progesterone is used as a raw material to prepare the cortisone acetate through bromine reaction, debromination reaction, bromination reaction, replacement reaction and oxidation reaction. The method can effectively avoid the occurrence of side reactions, and improves the quality of the product; at the same time, iodine is replaced by low-cost bromine for halogenating reaction, the production cost is greatly reduced, the method is high in efficiency and low in energy consumption, and the product quality and yield are good.