trans-Ketoconazole

Base Information

• Chemical Name: trans-Ketoconazole
• CAS No.: 83374-59-8
• Molecular Formula: C₂₆H₂₈Cl₂N₄O₄
• Molecular Weight: 531.439
• Hs Code.: 29349990
• UNII: 3INP7D7XI3,2EWW9YYR6A
• ChEMBL ID: CHEMBL328863
• Metabolomics Workbench ID: 56950
• Nikkaji Number: J220.792C
• Wikidata: Q27121165
• Mol file: 83374-59-8.mol

Synonyms:trans-Ketoconazole;83374-59-8;(2R,4R)-ketoconazole;Ketoconazole, trans-;rac-trans-Ketoconazole;Ketoconazole, trans-(+/-)-;3INP7D7XI3;RS-36745;CHEMBL328863;142128-58-3;CHEBI:48344;R-44319;1-[4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]piperazin-1-yl]ethanone;1-Acetyl-4-(4-(((2RS,4RS)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)piperazine;1-acetyl-4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine;Piperazine, 1-acetyl-4-(4-(((2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, rel-;Piperazine, 1-acetyl-4-(4-((2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl)methoxy)phenyl)-, trans-;Piperazine, 1-acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, rel-;UNII-3INP7D7XI3;(2R,4R)-trans-Ketoconazole;Ketoconazole impurity C [EP];2EWW9YYR6A;Ketoconazole, (2R,4R)-;HMS3869I03;BDBM50004441;CCG-36052;PD086247;KETOCONAZOLE IMPURITY C [EP IMPURITY];EN300-251596;Q27121165;(2R,4R)-1-acetyl-4-(4-{[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)piperazine;Piperazine, 1-acetyl-4-[4-[[(2R,4R)-2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-;Piperazine, 1-acetyl-4-[4-[[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy]phenyl]-, (2R-trans)-;rac-1-[4-(4-{[(2R,4R)-2-(2,4-dichlorophenyl)-2-[(1H-imidazol-1-yl)methyl]-1,3-dioxolan-4-yl]methoxy}phenyl)piperazin-1-yl]ethan-1-one

Chemical Property of trans-Ketoconazole

Chemical Property:

• PSA: 69.06000
• LogP: 4.20870
• XLogP3: 4.3
• Hydrogen Bond Donor Count: 0
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 7
• Exact Mass: 530.1487608
• Heavy Atom Count: 36
• Complexity: 735

Purity/Quality:

97% ^*data from raw suppliers

rac-trans-Ketoconazole ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OCC3COC(O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Isomeric SMILES: CC(=O)N1CCN(CC1)C2=CC=C(C=C2)OC[C@@H]3CO[C@](O3)(CN4C=CN=C4)C5=C(C=C(C=C5)Cl)Cl
• Uses: Ketoconazole (K186000) analog rac-trans-Ketoconazole (Ketoconazole EP Impurity C) is a Ketoconazole (K186000) analog. The trans isomer of Ketoconazole.

Technology Process of trans-Ketoconazole

There total 14 articles about trans-Ketoconazole 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:

ketokonazole → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With Beckman P/ACE MDQ Capillary Electrophoresis System equipped fused-silica capillaries (Polymicro Technologies, Phoenix, Arizona) of 50-μm ID cut with sulfobutyl ether β-cyclodextrin as chiral selector; In aq. buffer; at 25 ℃; pH=2.5; Concentration; pH-value; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/chir.22777

Reference yield:

ketoconazole (65277-42-1) → ketoconazole (65277-42-1) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7)

Guidance literature:

With cellulose (3,5-dimethylphenylcarbamate) coated reduced graphene oxide(at)silica gel; In hexane; at 25 ℃; enantioselective reaction; Resolution of racemate;

DOI:10.1002/chir.22976

Reference yield:

1-(4-{4-[2-(2,4-dichloro-phenyl)-2-imidazol-1-ylmethyl-[1,3]dioxolan-4-ylmethoxy]-phenyl}-piperazin-1-yl)-ethanone (79156-75-5) → ketoconazole (65277-42-1) + (2R,4R)-Ketoconazole (142128-58-3) + ketoconazole (65277-42-1,72093-26-6,79156-75-5,83374-59-8,142128-57-2,142128-58-3,142128-59-4,142128-60-7) + (2S,4S)-Ketoconazole (142128-60-7)

Guidance literature:

With methanol; sodium dodecyl-sulfate; 2,3,6-trimethyl-beta-cyclodextrin; sodium hydroxide; In aq. phosphate buffer; at 25 ℃; pH=2.5; pH-value; Reagent/catalyst; Temperature; Resolution of racemate;

DOI:10.1002/chir.22416

upstream raw materials:

trans-<2-(2,4-Dichlorophenyl)-2-<1H-imidazol-1-yl>methyl-(1,3-dioxolan-4-yl)>methyl methanesulfonate

N-acetyl-N'-(4-hydroxyphenyl)piperazine

1-(4-hydroxy-phenyl)-piperazine dihydrobromide

1-(4-Acetoxyphenyl)-4-acetylpiperazine

Downstream raw materials:

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-difluoromethanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-trifluoromethanesulfonylpiperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(oxane-4-sulfonyl)piperazine

1-(4-{[(2S,4R)-2-(2,4-dichlorophenyl)-2-(imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methoxy}phenyl)-4-(2-methoxyethanesulfonyl)piperazine