9,11-Dehydrodexamethasone acetate

Base Information

• Chemical Name: 9,11-Dehydrodexamethasone acetate
• CAS No.: 10106-41-9
• Molecular Formula: C24H30 O5
• Molecular Weight: 398.499
• European Community (EC) Number: 233-290-4
• UNII: AOW1NH1RMD
• DSSTox Substance ID: DTXSID80862466
• Nikkaji Number: J227.036F
• Mol file: 10106-41-9.mol

Synonyms:10106-41-9;9,11-Dehydrodexamethasone acetate;Vamorolone acetate;AOW1NH1RMD;UNII-AOW1NH1RMD;17-alpha,21-Dihydroxy-16-alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-acetate;[2-[(8S,10S,13S,14S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-7,8,12,14,15,16-hexahydro-6H-cyclopenta[a]phenanthren-17-yl]-2-oxoethyl] acetate;EINECS 233-290-4;17,21-Dihydroxy-16alpha-methylpregna-1,4,9(11)-triene-3,20-dione 21-Acetate;17-Hydroxy-16alpha-methyl-3,20-dioxopregna-1,4,9(11)-trien-21-yl Acetate;Pregnatriene acetate;SCHEMBL5708043;AMY7523;DTXSID80862466;Pregna-1,4,9(11)-triene-3,20-dione, 21-(acetyloxy)-17-hydroxy-16-methyl-, (16a)-;DEXAMETHASONE IMPURITY H [EP IMPURITY];DEXAMETHASONE ACETATE IMPURITY H [EP IMPURITY];Q27274041;(16alpha)-21-(Acetyloxy)-17-hydroxy-16-methylpregna-1,4,9(11)-triene-3,20-dione;17,21-Dihydroxy-16|A-methylpregna-1,4,9(11)-triene-3,20-dione 21-Acetate;17-HYDROXY-16.ALPHA.-METHYL-3,20-DIOXOPREGNA-1,4,9(11)-TRIEN-21-YL ACETATE;Pregna-1,4,9(11)-triene-3,20-dione, 17,21-dihydroxy-16.alpha.-methyl-, 21-acetate;PREGNA-1,4,9(11)-TRIENE-3,20-DIONE, 21-(ACETYLOXY)-17-HYDROXY-16-METHYL-, (16.ALPHA.)-

Chemical Property of 9,11-Dehydrodexamethasone acetate

Chemical Property:

• Vapor Pressure: 7.12E-15mmHg at 25°C
• Melting Point: 210-213 °C
• Boiling Point: 560°Cat760mmHg
• PKA: 12.48±0.70(Predicted)
• Flash Point: 189.6°C
• PSA: 80.67000
• Density: 1.22g/cm³
• LogP: 3.32370
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
• XLogP3: 2.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 4
• Exact Mass: 398.20932405
• Heavy Atom Count: 29
• Complexity: 880

Purity/Quality:

98%,99%, ^*data from raw suppliers

17,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione21-Acetate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1CC2C3CCC4=CC(=O)C=CC4(C3=CCC2(C1(C(=O)COC(=O)C)O)C)C
• Isomeric SMILES: C[C@@H]1C[C@H]2[C@@H]3CCC4=CC(=O)C=C[C@@]4(C3=CC[C@@]2([C@]1(C(=O)COC(=O)C)O)C)C
• Uses: 17,21-Dihydroxy-16α-methylpregna-1,4,9(11)-triene-3,20-dione 21-Acetate is an intermediate in the synthesis of Mometasone Furoate (M490000), a tropical corticosteroid used as an anti-inflammatory agent.

Technology Process of 9,11-Dehydrodexamethasone acetate

There total 37 articles about 9,11-Dehydrodexamethasone acetate which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.2%

C25H29NO3 → 17α,21-dihydroxy-16α-methyl-1,4,9(11)-pregnatriene-3,20-dione 21-acetate (10106-41-9)

Guidance literature:

With potassium permanganate; In ethylene glycol; acetone; at -10 ℃; for 6h;

Reference yield:

(Z)-2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate → 2-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (910-99-6,10106-41-9,98573-84-3)

Guidance literature:

With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 0 ℃; for 4h;

Reference yield:

2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate → 2-((10S,13S,16R,17R)-17-hydroxy-10,13,16-trimethyl-3-oxo-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (910-99-6,10106-41-9,98573-84-3)

Guidance literature:

2-((10S,13S,16R)-10,13,16-trimethyl-3-oxo-7,8,12,13,15,16-hexahydro-3H-cyclopenta[a]phenanthren-17(6H,10H,14H)-ylidene)-2-(trimethylsilyloxy)ethyl acetate; With peracetic acid; In acetic acid; toluene; at -10 ℃;

With sodium hydrogensulfite; trifluoroacetic acid;

DOI:10.1016/j.bmc.2013.02.009

upstream raw materials:

2-((10S,13S)-10,13-dimethyl-3-oxo-6,7,8,10,12,13,14,15-octahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate

21-acetoxy-17-hydroxy-16α-methyl-5α-pregn-9(11)-ene-3,20-dione

21-acetoxy-17-hydroxy-16α-methyl-11α-(toluene-4-sulfonyloxy)-pregna-1,4-diene-3,20-dione

acetic anhydride

Downstream raw materials:

betamethasone

(10S,13S,16R,17R)-17-hydroxy-17-(2-hydroxyacetyl)-10,13,16-trimethyl-6,7,8,10,12,13,14,15,16,17-decahydro-3H-cyclopenta[a]phenanthren-3-one

9α-chloro-16α-methyl-11β,17α,21-trihydroxy-1,4-pregnadiene-3,20-dione 17-(2'-furoate) 21-acetate

C₂₇H₃₁ClO₇

Refernces

• 1、 -. "AQUEOUS ORAL PHARMACEUTICAL SUSPENSION COMPOSITIONS". . . Retrieved 2020/09/22.
• 2、 Das, Saibal Kumar,Dubey, Manoj Kumar,Buchhikonda, Ravinder. "Improvements in corticosteroid 21-acetoxy-17α-hydroxy-16α-methyl-pregna-1,4,9(11)-triene-3,20-dione synthesis and its use as common intermediate in the synthesis of some impurities related to dexamethasone and mometasone". . p. 47 - 55. Retrieved 2019/05/22.