3044-42-6

Basic information

• Product Name: 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate
• Synonyms: 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate;21-Acetyloxy-11β-hydroxypregna-1,4,16-triene-3,20-dione;21-acetoxy-11β-hydroxypregna-1,4,16-triene-3,20-dione;Pregna-1,4,16-triene-3,20-dione,21-(acetyloxy)-11-hydroxy-, (11b)-;[2-[(8S,9S,10R,11S,13S,14S)-11-Hydroxy-10,13-Dimethyl-3-Oxo-6,7,8,9,11,12,14,15-Octahydrocyclopenta[a]Phenanthren-17-Yl]-2-Oxoethyl] Acetate;21-Acetoxy-112-hydroxypregna-1,4,16-triene-3,20-dione
• CAS NO: 3044-42-6
• Molecular Formula: C₂₃H₂₈O₅
• Molecular Weight: 384.46542
• EINECS: 221-250-9
• Mol File: 3044-42-6.mol
• Article Data: 18

Chemical Properties

• Melting Point: 208-209 °C
• Boiling Point: 553.4°Cat760mmHg
• Flash Point: 189.9°C
• Appearance: /
• Density: 1.24g/cm³
• Vapor Pressure: 1.5E-14mmHg at 25°C
• Refractive Index: 1.584
• Solubility: DCM, Ethyl Acetate
• PKA: 14.30±0.70(Predicted)
• CAS DataBase Reference: 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate(CAS DataBase Reference)
• NIST Chemistry Reference: 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate(3044-42-6)
• EPA Substance Registry System: 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate(3044-42-6)

Safety Data

• Hazardous Substances Data: 3044-42-6(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate is used as an intermediate in the synthesis of Budesonide (B689490) and its related derivatives. Budesonide is a corticosteroid medication used to treat various inflammatory conditions, such as asthma, allergic rhinitis, and skin disorders. 11beta,21-dihydroxypregna-1,4,16-triene-3,20-dione 21-acetate's role in the synthesis process is essential for producing effective and potent corticosteroid drugs that can alleviate symptoms and improve the quality of life for patients suffering from these conditions.

InChI:InChI=1/C23H28O5/c1-13(24)28-12-20(27)18-7-6-17-16-5-4-14-10-15(25)8-9-22(14,2)21(16)19(26)11-23(17,18)3/h7-10,16-17,19,21,26H,4-6,11-12H2,1-3H3/t16-,17-,19-,21+,22-,23-/m0/s1

Upstream product

• 52-21-1 prednisolone 21-acetate 
• 53512-79-1 11-trimethylsilyl ether prednisolone acetate 
• 17652-24-3 prednisolone 17,21-diacetate 
• 6677-19-6 17α,21-diacetoxypregna-1,4-diene-3,11,20-trione 
• 125-10-0 prednisone acetate 
• 137759-51-4 C₂₅H₃₄O₆ 
• 52628-64-5 prednisolone Acetate 
• 50-24-8 prednisolon 

Downstream Products

• 86401-80-1 11β,16α,17α,21-tetrahydroxypregnane-1,4-diene-3,20-dione-21-acetate 
• 1323941-30-5 (4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-Benzyl-5-hydroxy-6b-(2-hydroxy-acetyl)-4a,6a-dimethyl-4b,5,6,6a,6b,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-2-one 
• 1323941-13-4 Acetic acid 2-((4aR,4bS,5S,6aS,6bS,9aR,10aS,10bS)-8-benzyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4b,5,6,6a,7,8,9,9a,10,10a,10b,11,12-tetradecahydro-4aH-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester 
• 111802-47-2 methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate 
• 111802-43-8 methyl 11β,21-dihydroxy-3,20-dioxo-1,4-pregnadiene-16α-carboxylate 
• 83291-83-2 Acetic acid 2-((4aR,4bS,5S,6aS,6bR,9aS,10aS,10bS)-8-benzyl-5-hydroxy-4a,6a-dimethyl-2-oxo-2,4a,4b,5,6,6a,8,9,9a,10,10a,10b,11,12-tetradecahydro-7-oxa-8-aza-pentaleno[2,1-a]phenanthren-6b-yl)-2-oxo-ethyl ester 

Relevant articles and documents

Preparation method and application of 16, 17-dihydroxy steroid compound

The invention provides a preparation method and application of a 16, 17-dihydroxy steroid compound, and relates to the technical field of chemical synthesis. The method comprises the steps of: (a) reacting a compound shown as a formula I, lewis acid and an azole compound to obtain a compound shown as a formula II; and (b) reacting the compound as shown in the formula II, cyclic acyl peroxide and water, and then hydrolyzing under an alkaline condition to obtain a compound as shown in a formula III. Lewis acid and an azole compound are used in the dehydration reaction of the compound shown in the formula I, the operation is easy, the reaction conditions are mild, the energy cost is low, and the safety coefficient is high. The cyclic acyl peroxide is used in the oxidation reaction of the compound shown in the formula II, so that the method is good in atom economy, few in side reaction, free of excessive impurities, easy to implement and repeat, free of heavy metal participation, green, environment-friendly, safer and good in application prospect.

9-site dehalogenation method of steroid compound

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Novel method for preparing 16a-alpha-hydroxy prednisonlone product

The invention provides a novel method for preparing a 16a-alpha-hydroxy prednisonlone product. The method includes the steps: A protector preparation: performing 11-position silicon etherification onprednisolone acetate and trimethylchlorosilane under catalysis of organic base to obtain a protector; B dewatering, hydrolysis deprotection and refining: performing 17-position dewatering reaction onthe protector and SO3 under catalysis of organic base, performing acid addition treatment after reaction, and enabling 11 position to perform deprotection to obtain 17a-prednisolone dehydroxyacetate;C taking the 17a-prednisolone dehydroxyacetate as a raw material to prepare a 16a-alpha-hydroxy prednisonlone crude product, and refining the crude product to obtain the 16a-alpha-hydroxy prednisonlone product. The novel method solves the problems that traditional production technology of the 17a-prednisolone dehydroxyacetate is more in side reaction and impurity, impurities cannot be accurately refined and the like. The total yield of synthesis of the 16a-alpha-hydroxy prednisonlone is greatly improved, and production cost is reduced.

Preparation method of 17a-dehydroxy prednisolone acetate

The invention provides a preparation method of 17a-dehydroxy prednisolone acetate. The method includes the following steps: step A, dissolving prednisolone acetate as a raw material in a first organicsolvent, and subjecting the solvent and trimethylchlorosilane to 11th-position silicon etherification reaction under the catalysis of organic base for selective protection of 11th-position hydroxy toobtain a protector; step B, in a second organic solvent, subjecting the protector and SO3 to 17th-position dehydration reaction under the catalysis of the organic base, directly adding acid for treatment after the reaction to deprotect the 11th position, and obtaining the 17a-dehydroxy prednisolone acetate. The preparation method has the advantages that the problems such as many side reactions and impurities and difficulty in impurity refining in the dehydration reaction in a traditional production process of the 17a-dehydroxy prednisolone acetate are solved, the total synthesis yield is remarkably increased, and the production cost is reduced.

Preparation method of 17a-dehydroxy prednisolone acetate product

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New method for preparing 16alpha-hydroxyprednisolone

The invention provides a new method for preparing 16alpha-hydroxyprednisolone. The method comprises the following steps that A, a protector is prepared, wherein prednisolone acetate and trimethylchlorosilane are catalyzed by organic base to generate a 11th-site silicon etherification reaction, and then the protector is obtained; B, dehydration, hydrolysis deprotection and refining are conducted, wherein the protector and SO3 are catalyzed by organic base to generate a 17th-site dehydration reaction, after the reaction, acid is directly added to make the 11th site deprotected, and a crude 17alpha-dehydroxylated prednisolone acetate product is obtained; the crude product is refined to obtain a 17alpha-dehydroxylated prednisolone acetate product; C, the 17alpha-dehydroxylated prednisolone acetate product is used as a raw material to prepare the 16alpha-hydroxyprednisolone. The problems are solved that in a traditional production technology of the 17alpha-dehydroxylated prednisolone acetate, more side reactions and impurities are generated in the dehydration process, and the impurities are difficult to refine; the total yield of the synthesized 16alpha-hydroxyprednisolone is greatly improved, and the production cost is reduced.

ISOXAZOLIDINE DERIVATIVES

Anti-inflammatory and antiallergic compounds of the glucocorticosteroid series, according to formula (I) according to formula (I) defined herein are useful for treating diseases of the respiratory tract characterized by airway obstruction.

ISOXAZOLIDINE DERIVATIVES

The present invention relates to novel anti-inflammatory and antiallergic compounds of the glucocorticosteroid series, methods of preparing such compounds, pharmaceutical compositions comprising them, combinations and therapeutic uses thereof. More particularly, the invention relates to glucocorticosteroids that are derivatives of isoxazolidine.

ISOXAZOLIDINE DERIVATIVES

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