(R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid: Synthesis Attempts and Failure Report

(R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid is a chiral, sulfonated aromatic compound featuring a catechol (ortho-dihydroxybenzene) core substituted with a side chain containing a secondary methylamino group and a hydroxyl group.

EMA Guidance on Nitrosamines

According to EMA guidelines, if repeated synthesis attempts fail to detect the formation of nitrosamine impurities, it is likely that the impurity either does not exist or poses an extremely low risk.

Nitrosation

We conducted multiple nitrosation assays under rigorous forced conditions (NAP tests), to evaluate the risk of (R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid formation. Our findings revealed that (R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid does not readily undergo nitrosation under the expected conditions, significantly reducing concerns about its potential formation.

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Our synthesis failure report provides a detailed account of the findings from our synthesis attempts and rigorous testing, demonstrating the non-formation of the nitroso impurity. It offers a comprehensive overview of the evaluated conditions and the resulting data.

(R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid Technical Information

• Molecular Weight: 263.27 g/mol
• Molecular Formula: C9H13NO6S
• IUPAC Name: (R)-2,3-dihydroxy-5-(1-hydroxy-2-(methylamino)ethyl)benzenesulfonic acid
• CAS Number: N/A
• Synonyms: N/A

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