cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate, CAS No. 134071-44-6

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134071-44-6

Catalog No. EBD33690

CAS 134071-44-6

Name cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate

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Basic Information

Synonyms: (2R,4R)Cis-(2,4-Dichlorophenyl)-2-(1,2,4-Triazole-1-Yl-Methyl)-1,3-Dioxolane-4Yl-Methyl-P-Tolysulfonate Cis-[2,4-Dichlorophenyl)-2-(1H-Imidazol-1-Ylmethyl)-1,3-Dioxalan-4-Yl]Methyl-P-Tolysulfonate Cis-2-(2,4-Dichlorophenyl)-2-(1H-Imidazole-1-Yl)Methyl-4-(P-TolueneSulfonyloxy)Methyl-1,3-Dioxalane Cis-[2-(2,4-Dichlorophenyl)-2-(1H-Imidazol-YlMethyl)-1,3-Dioxolane-4-Yl]-P-MethylbenzeneSulfonate ActivityEsterofKetoconazol Cis-[2-(2,4-Dichlorophenyl)-2-(1H-Imidazol-YlMethyl)-1,3-Dioxolane-4-Yl]-P-MethylbenzeneSulfonateOr-P-MethylSulfonate(KetoconazleIntermediate) [(2S,4S)-2-(2,4-Dichlorophenyl)-2-(1H-1,2,4-Triazol-1-Ylmethyl)-1,3-Dioxolan-4-Yl]Methyl4-Methylbenzenesulfonate cis-[2-(2,4-Dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl-4-methylbenzenesulphonate cis-[2-(2,4-dich

Molecular Formula: C21H20Cl2N2O5S

Molecular Weight: 483.36

MDL Number: MFCD00800225

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates

Product Description:

Cis-[2-(2,4-dichlorophenyl)-2-(1H-imidazol-1-ylmethyl)-1,3-dioxolan-4-yl]methyl 4-methylbenzenesulfonate is a key chiral intermediate in the synthesis of the broad-spectrum antifungal agent, Sertaconazole. Its structure features a 1,3-dioxolane ring fused with an imidazole moiety and a 2,4-dichlorophenyl group, which are pharmacophores critical for antifungal activity. The compound contains a tosylate leaving group, which is pivotal for subsequent nucleophilic substitution reactions in the synthetic pathway. This intermediate is specifically designed for the industrial production of Sertaconazole nitrate, a potent imidazole antifungal drug used topically to treat cutaneous fungal infections such as tinea pedis, tinea corporis, and candidiasis. The synthesis of this intermediate involves stereoselective methods to obtain the desired cis-isomer, which is essential for the biological efficacy of the final API. Its primary and almost exclusive application is within pharmaceutical manufacturing as a high-value building block. Handling of this compound requires standard precautions for fine chemicals, including the use of personal protective equipment due to its potential irritant properties. As a specialized synthetic intermediate, it is not intended for direct therapeutic use and is primarily of interest to pharmaceutical research and development organizations and API manufacturers.

Physical Properties

Melting Point: 120-122 °C

Boiling Point: 665.674 °C at 760 mmHg

Flash Point: 356.387 °C

Density: 1.444 g/cm3

Analytical Data

Appearance: Off-white solid