Home / Products / (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide
CAS 521284-19-5 Mirabegron EP Impurity G Mirabegron EP Impurity G High Purity USP Grade EP Grade BP Grade JP Grade Reference Standard

(R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide

IUPAC: (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide View on PubChem
CAS NUMBER
521284-19-5
MOL. FORMULA
C16H16N2O4
MOL. WEIGHT
300.31 g/mol
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Scientific Overview

This compound sits directly upstream of the amino-alcohol intermediate ((R)-2-((4-Aminophenethyl)amino)-1-phenylethan-1-ol) in the mirabegron synthetic pathway: reduction of its nitro group to an amine, coupled with reduction of the amide carbonyl to an amine linkage, generates that downstream intermediate. As a fully characterized reference material compliant with USP, EMA, JP, and BP standards, it is essential for supporting ANDA and NDA regulatory submissions and commercial mirabegron production quality control.

(R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide, designated Mirabegron EP Impurity G (also known as Mirabegron INT 1), is a chiral hydroxyamide bearing a nitrophenyl substituent that serves as a key upstream synthetic intermediate in the manufacturing route to mirabegron, a selective ß3-adrenergic receptor agonist indicated for overactive bladder syndrome.

Full Technical Data
Chemical Name (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide (Mirabegron EP Impurity G)
CAS Number 521284-19-5
IUPAC Name (R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide
Molecular Formula C16H16N2O4
Molecular Weight 300.31 g/mol g/mol
Reaction Scheme
(R)-Mandelic Acid (or activated derivative)
4-Nitrophenethylamine
NA
(R)-2-Hydroxy-N-(4-nitrophenethyl)-2-phenylacetamide
NA
Commercial Applications

Mirabegron API Manufacturing

Direct upstream synthetic intermediate in the multi-step industrial route to mirabegron.

Pharmacopeial Impurity Reference Standard

Designated Mirabegron EP Impurity G for European Pharmacopoeia-compliant drug substance quality control.

Regulatory Submission Support

Used in ANDA and NDA filings requiring characterized impurity reference materials for mirabegron.

Analytical Method Development

Supports HPLC method validation for mirabegron process impurity monitoring.

Market Therapeutic Focus
MIRABEGRON EP IMPURITY G PHARMACEUTICAL MANUFACTURING UROLOGY / OVERACTIVE BLADDER THERAPEUTICS ANALYTICAL REFERENCE STANDARDS API PROCESS CHEMISTRY CRO/CDMO
Scientific Literature

Mirabegron: A Review of its Use in Overactive Bladder Syndrome

Authors: Cui, Y. et al.

Drugs

DOI: 10.1007/s40265-014-0287-9

Synthesis and Structure-Activity Relationships of ß3-Adrenergic Receptor Agonists

Authors: Ohtake, Y. et al.

J. Med. Chem.

DOI: 10.1021/jm300148g

Process Chemistry and Impurity Control Strategy for Mirabegron Manufacturing

Authors: Various

Org. Process Res. Dev. (process chemistry reference)

Peer Queries & FAQs
How does this compound relate to mirabegron?
It's an upstream synthetic intermediate; sequential reduction of its nitro and amide functional groups yields the aminoalcohol intermediate that is further coupled with a thiazole fragment to complete mirabegron's structure.
Why is this designated an "impurity" if it's also an intermediate?
In pharmaceutical manufacturing, synthetic intermediates that could persist as residual impurities in the final API are formally classified and monitored as named impurities per regulatory guidelines --- hence its dual role as process intermediate and EP Impurity G.
What regulatory standards does this reference material meet?
It is characterized to comply with USP, EMA, JP, and BP requirements, making it suitable for global regulatory submissions.
What is the recommended storage condition?
Store in a refrigerator (2--8°C) for long-term storage, protected from light and moisture.

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