Desmethylmifepristone

Base Information

• Chemical Name: Desmethylmifepristone
• CAS No.: 104004-96-8
• Molecular Formula: C28H33 N O2
• Molecular Weight: 415.576
• Hs Code.: 9999999999
• European Community (EC) Number: 835-959-1
• UNII: K1P8OGJ86J
• DSSTox Substance ID: DTXSID60146216
• Nikkaji Number: J386.665C
• Wikipedia: Metapristone
• Wikidata: Q27281827
• Pharos Ligand ID: 3TLVSNCS7SDN
• Metabolomics Workbench ID: 144748
• ChEMBL ID: CHEMBL1608
• Mol file: 104004-96-8.mol

Synonyms:Ru 42633;RU-42633

Chemical Property of Desmethylmifepristone

Chemical Property:

• Vapor Pressure: 1.11E-16mmHg at 25°C
• Melting Point: 83-86°C
• Boiling Point: 628.9°Cat760mmHg
• PKA: 12.94±0.60(Predicted)
• Flash Point: 334.1°C
• PSA: 49.33000
• Density: 1.19g/cm³
• LogP: 5.45520
• Storage Temp.: -20°C Freezer
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 3.6
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 3
• Rotatable Bond Count: 3
• Exact Mass: 415.251129295
• Heavy Atom Count: 31
• Complexity: 893

Purity/Quality:

98%Min ^*data from raw suppliers

N-DemethylMifepristone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC#CC1(CCC2C1(CC(C3=C4CCC(=O)C=C4CCC23)C5=CC=C(C=C5)NC)C)O
• Isomeric SMILES: CC#C[C@@]1(CC[C@@H]2[C@@]1(C[C@@H](C3=C4CCC(=O)C=C4CC[C@@H]23)C5=CC=C(C=C5)NC)C)O
• Uses: A metabolite of Mifepristone (M343975).

Technology Process of Desmethylmifepristone

There total 6 articles about Desmethylmifepristone 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: 97.0%

mifepristone (84371-65-3) → (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-(methylamino)phenyl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (104004-96-8)

Guidance literature:

With lithium acetate; iodine; In tetrahydrofuran; methanol; at 0 - 20 ℃; for 24h; Reagent/catalyst; Temperature; Solvent;

DOI:10.1039/c5ra26557f

Reference yield: 86.0%

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylformamide (639520-83-5) → (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-(methylamino)phenyl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (104004-96-8)

Guidance literature:

With hydrogenchloride; In methanol; at 20 ℃; for 40h;

DOI:10.1021/jm0400045

Reference yield: 74.0%

tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate (639520-75-5) → (8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-11-(4-(methylamino)phenyl)-17-(prop-1-yn-1-yl)-1,2,6,7,8,11,12,13,14,15,16,17-dodecahydro-3H-cyclopenta[a]phenanthren-3-one (104004-96-8)

Guidance literature:

tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate; With toluene-4-sulfonic acid; In tetrahydrofuran; dichloromethane; at 20 ℃; for 3h;

With sodium hydrogencarbonate; In tetrahydrofuran; dichloromethane; water; at 25 ℃;

upstream raw materials:

11β-(4-methylaminophenyl)-<3,3-(1,2-ethylenedioxybisoxy)>-17α-(1-propynyl)-estra-9-en-5α,7β-diol

mifepristone

N-(4-((8S,11R,13S,14S,17S)-17-hydroxy-13-methyl-3-oxo-17-(prop-1-yn-1-yl)-2,3,6,7,8,11,12,13,14,15,16,17-dodecahydro-1H-cyclopenta[a]phenanthren-11-yl)phenyl)-N-methylformamide

tert-butyl 4-((5R,11R,13S,17S)-5,17-dihydroxy-13-methyl-17-prop-1-ynyl-1,2,4,5,6,7,8,11,12,13,14,15,16,17-tetradecahydrospiro[cyclopenta[a]phenanthrene-3,2'-[1,3]dioxolan]-11-yl)phenyl(methyl)carbamate

Downstream raw materials:

C₅₆H₉₁NO₈Si₃

11β-{4-((4(S)-t-Butoxycarbonylamino-4(S)-methoxycarbonyl)butyryl-methyl-amino)phenyl}-17β-hydroxy-17α-(1-propynyl)estra-4,9-dien-3-one