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

21-Acetoxy-11β-hydroxypregna-1,4,16-triene-3,20-dione is an intermediate in the synthesis of Budesonide (B689490) related derivatives.

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

• 17652-24-3 prednisolone 17,21-diacetate 
• 52-21-1 prednisolone 21-acetate 
• 53512-79-1 11-trimethylsilyl ether prednisolone acetate 
• 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

• 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 
• 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 

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.

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 product

The invention provides a preparation method of a 17a-dehydroxy prednisolone acetate product. The method includes the following steps: step A, dissolving prednisolone acetate in a first organic solvent, and subjecting the solvent and trimethylchlorosilane to 11th-position silicon etherification reaction under the catalysis of organic base to obtain 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 a crude 17a-dehydroxy prednisolone acetate product; subjecting the crude product to decolorization and recrystallization in the presence of C4-below low carbon alcohol and activated carbonto obtain the 17a-dehydroxy prednisolone acetate product. The preparation method has the advantages that the problems such as many side reactions and impurities and difficulty in impurity refining inthe dehydration reaction in a traditional production process of 17a-dehydroxy prednisolone acetate are solved, the total synthesis yield is remarkably increased, and the production cost is reduced.