Methyl prednisolone-16alpha-carboxylate

Base Information

• Chemical Name: Methyl prednisolone-16alpha-carboxylate
• CAS No.: 111802-47-2
• Molecular Formula: C₂₃H₃₀O₇
• Molecular Weight: 418.487
• DSSTox Substance ID: DTXSID60920573
• Nikkaji Number: J533.144G
• Wikidata: Q27120841
• Metabolomics Workbench ID: 56825
• Mol file: 111802-47-2.mol

Synonyms:6-methoxycarbonyl prednisolone;6-methoxycarbonylprednisolone;methyl 11 beta,17 alpha,21-trihydroxy-1,4-pregnadiene-3,20-dione-16-carboxylic acid;methyl 11,17,21-trihydroxy-3,20-dioxopregna-1,4-diene-16-carboxylate;MTDPDC;TDPDC

Chemical Property of Methyl prednisolone-16alpha-carboxylate

Chemical Property:

• Vapor Pressure: 2.14E-17mmHg at 25°C
• Boiling Point: 609.4°Cat760mmHg
• Flash Point: 208.8°C
• PSA: 121.13000
• Density: 1.34g/cm³
• LogP: 0.95670
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 4
• Exact Mass: 418.19915329
• Heavy Atom Count: 30
• Complexity: 860

Purity/Quality:

99% ^*data from raw suppliers

P16CM 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC12CC(C3C(C1CC(C2(C(=O)CO)O)C(=O)OC)CCC4=CC(=O)C=CC34C)O
• Isomeric SMILES: C[C@]12C[C@@H]([C@H]3[C@H]([C@@H]1C[C@H]([C@@]2(C(=O)CO)O)C(=O)OC)CCC4=CC(=O)C=C[C@]34C)O

Technology Process of Methyl prednisolone-16alpha-carboxylate

There total 10 articles about Methyl prednisolone-16alpha-carboxylate 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: 56.0%

(8S,9S,10R,11S,13S,14S,16R)-11-Hydroxy-17-(2-hydroxy-acetyl)-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-16-carboxylic acid methyl ester → methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate (111802-47-2)

Guidance literature:

With peracetic acid; perchloric acid; acetic anhydride; Ambient temperature;

Reference yield: 8.0%

methanol (67-56-1) + Acetic acid 2-((8S,9S,10R,11S,13S,14S,16S,17R)-16-cyano-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester (17664-55-0) → methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate (111802-47-2) + (8S,9S,10R,11S,13S,14S,16R,17S)-17-(2,2-Dimethoxy-acetyl)-11-hydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthrene-16-carboxylic acid methyl ester (165403-42-9)

Guidance literature:

With hydrogenchloride; 1.) -30 to -20 deg C, 1 d; 2.) -20 to -15 deg C, 4 h;

DOI:10.1016/0040-4039(95)00526-I

Reference yield:

prednisolon (50-24-8,8056-11-9) → methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate (111802-47-2)

Guidance literature:

Multi-step reaction with 9 steps

1: 1.) TsOH*py / benzene / Heating

2: 1.) 1percent acetic acid, 2.) pyridine / 1.) RT, 2.) RT

3: potassium acetate / dimethylformamide / 105 - 110 °C

4: 57 percent / NH₄Cl, 18-crown-6 / dimethylsulfoxide; H₂O / 0.5 h / 85 °C

5: 40.63 percent / 20percent HCl / dimethylsulfoxide / 5 h / Ambient temperature

6: 78 percent / pyridinium p-toluenesulfonic acid / CH₂Cl₂ / 4 h / Ambient temperature

7: 1.) NaOH, 2.) H₂SO₄ / 1.) H₂O, methanol, reflux, 2.5 h, 2.) methanol, reflux, 3 h

8: diethyl ether

9: 56 percent / HClO₄, Ac₂O, CH₃CO₃H / Ambient temperature

With pyridine; hydrogenchloride; peracetic acid; sodium hydroxide; perchloric acid; 18-crown-6 ether; sulfuric acid; potassium acetate; pyridinium p-toluenesulfonate; acetic anhydride; ammonium chloride; acetic acid; In diethyl ether; dichloromethane; water; dimethyl sulfoxide; N,N-dimethyl-formamide; benzene;

upstream raw materials:

methanol

Acetic acid 2-((8S,9S,10R,11S,13S,14S,16S,17R)-16-cyano-11,17-dihydroxy-10,13-dimethyl-3-oxo-6,7,8,9,10,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-17-yl)-2-oxo-ethyl ester

prednisolon

21-acetoxy-11β-hydroxyl-1,4,16-pregnatriene-3,20-dione

Refernces

• 1、 Taraporewala,Kim,Heiman,Lee. "A novel class of local antiinflammatory steroids. 1st Communication: Analogues of methyl 11β,17α,21-trihydroxy-3,20-dioxo-pregna-1,4-diene-16α-carboxylate". . p. 21 - 25. Retrieved 2007/10/02.