![CAS:376653-42-8 Phosphonium, [(3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, Bromide](/uploads/24095/cas-376653-42-85857c.png)
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name
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Phosphonium, ([3'R)-1'-[(1,1-dimethylethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenyl-, bromide)
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Synonyms
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([(3'R)-1'-[(1,1-Dimethyl - ethoxy)carbonyl]-2-oxo[1,3'-bipyrrolidin]-3-yl]triphenylphosphonium bromide)
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CAS
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376653-42-8
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MF
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C31H36BrN2O3P
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MW
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595.51
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Appearance and State
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Usually a white to off - white crystalline powder or solid at room temperature, odorless, with good crystallinity for purity ≥ 98% (pharmaceutical grade), and few or no visible impurities at low content.
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Solubility
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Easily soluble in polar organic solvents like dichloromethane, methanol, etc., slightly soluble in ethyl acetate and ether, difficult to dissolve in non - polar solvents and water (solubility < 1 g/L at 25°C).
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Melting Point and Thermal Stability
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Melting point 210 - 215°C (decomposition, DSC). Decomposes above melting point with color deepening. Stable when stored sealed and light - protected at 25°C, avoid high temp (> 80°C) and humidity to prevent hydrolysis or structure degradation.
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Optical Activity
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Chiral center (3'R - configuration), optical activity, specific rotation [α]₂₀ᴰ about +35° to +45° (c = 1, methanol), value varies with measurement, key for optical purity identification.
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Chemical Properties
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Quaternary phosphonium compound, contains Br⁻, ionic compound characteristics, dissociates in polar solvents, prone to hydrolysis under strong acid/base, store in neutral or weakly acidic environment, stable to air/oxygen, avoid strong oxidants/reductants.
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Other Properties
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Density about 1.32 - 1.38 g/cm³ (20°C, crystalline), no clear refractive index data (solid), non - flammable/explosive, no obvious corrosiveness, avoid skin/mucous membrane contact, wear protective gear.
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Usage
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Core Side Chain Raw Material for Ceftobiprole PivoxilAs a provider of critical functional fragments in the molecular structure of ceftobiprole pivoxil, it contains structural units such as chiral pyrrolidine rings and quaternary phosphonium salts, which are core components for constructing the cephalosporin nucleus and active side chain of ceftobiprole pivoxil. During the synthesis process, it undergoes condensation reactions with cephalosporin nuclei (e.g., 7-ACA-derived intermediates) to introduce specific antibacterial active groups, ultimately forming the complete chemical structure of ceftobiprole pivoxil. This directly determines the antibacterial activity of the final product against drug-resistant bacteria such as Methicillin-Resistant Staphylococcus Aureus (MRSA) and Vancomycin-Resistant Staphylococcus Aureus (VRSA).
Application as a Pharmaceutical-Grade High-Purity IntermediateIt is mainly used in the production of antibiotic active pharmaceutical ingredients (APIs) in the pharmaceutical industry, particularly suitable for the synthesis of clinical drugs such as ceftobiprole pivoxil injections and oral formulations. It must meet pharmaceutical-grade purity standards (typically ≥98% purity and ≥99% ee optical purity) to ensure that the synthesized ceftobiprole pivoxil complies with international quality specifications such as the United States Pharmacopeia (USP) and European Pharmacopeia (EP). It is applicable to scenarios such as new drug research and development, commercial production, and generic drug registration (e.g., ANDA, MAH applications) in pharmaceutical enterprises, serving as a key upstream raw material guaranteeing the quality and efficacy of ceftobiprole pivoxil drugs.
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