139264-55-4

Basic information

• Product Name: (S)-4-(4-Nitrobenzyl)-2-oxazolidinone
• Synonyms: (S)-4-(4-Nitrobenzyl)-2(1 H)-oxazolidinone;(S)-4-[(4-Nitrophenyl)methyl]-2-oxazolidinone
• CAS NO: 139264-55-4
• Molecular Formula: C₁₀H₁₀N₂O₄
• Molecular Weight: 222.1974
• Mol File: 139264-55-4.mol
• Article Data: 6

Chemical Properties

• Boiling Point: 509.509 °C at 760 mmHg
• Flash Point: 261.942 °C
• Appearance: /
• Density: 1.367
• Storage Temp.: 2-8°C
• PKA: 12.24±0.40(Predicted)
• CAS DataBase Reference: (S)-4-(4-Nitrobenzyl)-2-oxazolidinone(CAS DataBase Reference)
• NIST Chemistry Reference: (S)-4-(4-Nitrobenzyl)-2-oxazolidinone(139264-55-4)
• EPA Substance Registry System: (S)-4-(4-Nitrobenzyl)-2-oxazolidinone(139264-55-4)

Safety Data

• Hazardous Substances Data: 139264-55-4(Hazardous Substances Data)

Usage

Description

(S)-4-(4-Nitrobenzyl)-2-oxazolidinone is an organic compound that serves as an impurity in the synthesis of certain pharmaceutical compounds. It is characterized by its unique chemical structure, which includes a nitrobenzyl group attached to a 2-oxazolidinone ring.

Uses

Used in Pharmaceutical Synthesis:
(S)-4-(4-Nitrobenzyl)-2-oxazolidinone is used as an intermediate in the synthesis of various pharmaceutical compounds. Its presence as an impurity in the synthesis of 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan-d6 3-Acetic Acid (D288969) highlights its role in the production of this specific compound. (S)-4-(4-Nitrobenzyl)-2-oxazolidinone is the isotope labeled version of 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan 3-Acetic Acid (D288965), which is an indole acetic acid metabolite of Zolmitriptan (Z639000) formed by human hepatocytes.
In the pharmaceutical industry, (S)-4-(4-Nitrobenzyl)-2-oxazolidinone is used as a synthetic intermediate for the development of new drugs. Its application is crucial in the synthesis process, as it contributes to the formation of the desired active pharmaceutical ingredient (API). The compound's specific role in the synthesis of D288969 and D288965 demonstrates its importance in the development of medications targeting various health conditions.

Upstream product

• 75-44-5 phosgene 
• 89288-22-2 (S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 63-91-2 L-phenylalanine 
• 105-58-8 Diethyl carbonate 
• 17193-40-7 (S)-4-nitrophenylalanine methyl ester hydrochloride 
• 949-99-5 4-nitro-3-phenyl-L-alanine 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 

Downstream Products

• 1610608-12-2 (S)-3-((1S,2R)-1,2-diethyl-2-vinylcyclopropanecarbonyl)-4-(4-nitrobenzyl)oxazolidin-2-one 
• 1610608-07-5 (S)-3-((1R,2S)-1,2-diethyl-2-vinylcyclopropanecarbonyl)-4-(4-nitrobenzyl)oxazolidin-2-one 
• 139264-15-6 (S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine 
• 139264-57-6 (S)-4-(4-hydrazinobenzyl)-1,3-oxazolidin-2-one hydrochloride 
• 191864-24-1 ethyl 3-(2-dimethylaminoethyl)-5-[(4S)-2-oxooxazolidin-4-ylmethyl]-1H-indole-2-carboxylate 
• 152305-23-2 (S)-4-(4-aminobenzyl)-1,3-oxazolidin-2-one 
• 1020737-23-8 (4S)-4-(4-nitrobenzyl)-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 

Relevant articles and documents

Asymmetric synthesis of 3,3,5,5-tetrasubstituted 1,2-dioxolanes: Total synthesis of epiplakinic acid F

The first enantioselective total synthesis of epiplakinic acid F (1) was achieved through a pivotal step involving a radical-mediated asymmetric peroxidation of vinylcyclopropanes with molecular oxygen to construct highly substituted 1,2-dioxolanes. Subsequent conversions of the chiral 1,2-dioxolanes led to total synthesis of epiplakinic acid F (1) and the confirmation of its absolute configuration. The enantiomer of epiplakinic acid F methyl ester (2) was also prepared. This journal is the Partner Organisations 2014.

Design, synthesis, and evaluation of 4-(4′-aminobenzyl)-2-oxazolidinones as novel inhibitors of the cytochrome P-450 enzyme aromatase

The synthesis of a series of N-alkylated 4-(4′aminobenzyl)-2-oxazolidinones is described using a synthetically useful scheme which avoids the use of phosgene - since the derivatization is undertaken with the oxazolidin-2-one ring intact. The compounds were tested for human placental aromatase (AR) inhibition in vitro, using [1β, 2β-3H]androstenedione as substrate for the AR enzyme. The compounds were found, in general, to be more potent than the standard compound, amino-glutethimide (AG), and as such proved to be good lead compounds in the search for more specific AR inhibitors.

Computer-Aided Design and Synthesis of 5-Substituted Tryptamines and Their Pharmacology at the 5-HT1D Receptor: Discovery of Compounds with Potential Anti-Migraine Properties

The design and synthesis of a series of novel 5-substituted tryptamines with pharmacological activity at 5-HT1D and other monoamine receptors is described.Structural modifications of N- and C-linked (prinicipally hydantoin) analogues at the 5-position were synthesized and their pharmacological activities were utilized to deduce significant steric and electrostatic requirements of the 5-HT1D and 5-HT2A receptor subtypes.Conformations of the active molecules were computed which, when overlaid, suggested a pharmacophore hypothesis which was consistent with the affinity and selectivity measured at 5-HT1D and 5-HT2A receptors.This pharmacophore is composed of a protonated amine site, an aromatic site, a hydrophobic pocket, and two hydrogen-bonding sites.A 'selectively site' was also identified which, if occupied, induced selectivity for 5-HT1D over 5-HT2A in this series of molecules.The development and use of the pharmacophore models in compound design is described.In addition, the physicochemical constraints of molecular size and hydrophobicity required for efficient oral absorption are discussed.Utilizing the pharmacophore model in conjuction with the physicochemical constraints of molecular size and log DpH7.4 led to the discovery of 311C90 (6), a new selective 5-HT1D agonist with good oral absorption and potential use in the treatment of migraine.