Linezolid mesylate ester
Linezolid mesylate ester (CAS 174649-09-3), also known as linezolid related compound D, Linezolid USP Related Compound D or (R)-[3-(3-fluoro-4-morpholinophenyl)-2-oxooxazolidin-5-yl]methyl methanesulfonate, is a white to off-white crystalline solid supplied at 99 percent purity in quantities ranging from ten milligrams to several grams. It is the mesylate ester of the oxazolidinone alcohol at the heart of the antibiotic linezolid, an activated intermediate in which the methanesulfonate group serves as a leaving group for nucleophilic substitution. Stored dry at room temperature it is stable, but it is moisture and heat sensitive over long periods and should be protected from bases that could promote elimination. It is used both as a manufacturing process intermediate and as an analytical reference substance.
1. Antibiotic process intermediate: the penultimate, activated oxazolidinone used in the manufacture of linezolid, a synthetic antibacterial effective against resistant gram-positive organisms such as methicillin-resistant Staphylococcus aureus and vancomycin-resistant enterococci.
2. Reference standard: because it is a specified related substance of linezolid it serves as a pharmacopoeial and in-house reference standard for impurity identification, chromatographic method validation, relative response factor determination and routine quality control of drug substance and tablets.
3. Mechanism relevance: the mesylate leaving group allows introduction of the azide or amine functionality that completes the linezolid structure, illustrating the classic activation-substitution sequence used in oxazolidinone chemistry and in the design of synthetic routes.
4. Handling and storage: keep in a tightly closed container in a dry, cool place away from strong nucleophiles, bases and oxidising agents; as a mesylate ester with alkylating potential it should be handled with adequate containment, eye protection and local ventilation, avoiding dust inhalation.
Product Name: Linezolid mesylate ester
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