(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one, CAS No. 189028-95-3

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189028-95-3

Catalog No. EBD5834

CAS 189028-95-3

Name (4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one

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Basic Information

Synonyms: (4S)-3-[(5R)-5-(4-FLUOROPHENYL)-5-HYDROXYPENTANOYL]-4-PHENYL-1,3-OXAZOLIDIN-2-ONE 2-Oxazolidinone,3-[(5S)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-,(4S)- (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one (S)-3-((S)-5-(4-fluorophenyl)-5-hydroxypentanoyl)-4-phenyloxazolidin-2-one (4s)-3-[(5s)-5-(4-fluorophenyl)-5-hydroxy-1-oxo-pentyl]-4-phenyl-2-oxazolidinone ezetimibeintermediates 3-[(5s)-5-(4-fluorophenyl)-5-hydroxy-1-oxopentyl]-4-phenyl-,(4s)-2-oxazolidinone ezetimibeinta (4S)-4-Phenyl-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-1,3-oxazolidin-2-one (4S)-3-[(5S)-5-(4-fluorophenyl)-5-hydroxypentanoyl]-4-phenyl

Molecular Formula: C20H20FNO4

Molecular Weight: 357.38

MDL Number: MFCD13194798

Categories: Medicinal Chemistry > Pharmaceutical Intermediates > Heterocyclic Intermediates Medicinal Chemistry > APIs and Their Salts > Cardiovascular Drugs

Product Description:

(4S)-3-[(5S)-5-(4-Fluorophenyl)-5-hydroxypentanoyl]-4-phenyl-1,3-oxazolidin-2-one is a chiral oxazolidinone derivative. It serves as a crucial chiral auxiliary and synthetic intermediate in the production of active pharmaceutical ingredients (APIs). Its structure features a 4-fluorophenyl and a phenyl group attached to a core oxazolidin-2-one ring, which is a common scaffold for imparting stereochemical control in asymmetric synthesis. This compound is primarily recognized as a key intermediate in the synthesis of (S)-Duloxetine, a widely prescribed serotonin-norepinephrine reuptake inhibitor (SNRI) used for the treatment of major depressive disorder, generalized anxiety disorder, and certain types of chronic pain like fibromyalgia and diabetic peripheral neuropathy. The specific stereochemistry (4S,5S) of this intermediate is essential for constructing the desired (S)-enantiomer of Duloxetine, which possesses the required pharmacological activity. The use of this chiral oxazolidinone auxiliary allows for highly enantioselective transformations during the API manufacturing process, ensuring the production of the therapeutically active isomer with high purity. Its application underscores its importance in the streamlined and stereocontrolled synthesis of complex, chiral drug molecules within the pharmaceutical industry.

Physical Properties

Boiling Point: 572.727 °C at 760 mmHg

Flash Point: 300.174 °C

Density: 1.297