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

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

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 
• 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 
• 32315-10-9 bis(trichloromethyl) carbonate 
• 90719-32-7 (S)-4-Benzyl-2-oxazolidinone 

Downstream Products

• 1020737-23-8 (4S)-4-(4-nitrobenzyl)-3-[(2E)-3-phenylprop-2-enoyl]-1,3-oxazolidin-2-one 
• 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 

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.

AN IMPROVED PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN

Disclosed herein the process for producing pure" Zolmitriptan employing improved reaction conditions which excluded the use of column chromatography.

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.

A novel series of 2,5-substituted tryptamine derivatives as vascular 5HT(1B/1D) receptor antagonists

The design, synthesis, and activity of a novel series of 2,5- substituted tryptamine derivatives at vascular 5HT(1B)-like receptors is described. Several important auxiliary binding sites of the 5HT(1B)-like receptor have been proposed following various modifications to the 2- substituent and especially to the methylene- or ethylene-linked 5-side chain. Careful design of new molecules based on a proposed pharmacophoric model of the 5HT(1B)-like receptor has resulted in the discovery of ethyl 3-[2- (dimethylamino)ethyl]-5-[2-(2,5-dioxo-1-imidazolidinyl)ethyl]-1H-indole-2- carboxylate (40), a highly potent, silent, competitive, and selective antagonist which shows affinity at the vascular 5HT(1B)-like receptors only. Changes to the size of the 2-ester substituent have a significant effect on affinity at the 5HT(1B)-like receptor and other receptors. Prudent placement of the carbonyl substituent in the heterocycle of the 5-side chain is crucial for good affinity and selectivity over the 5HT(2A) and other receptors. Several key structural and electronic features were identified which are crucial for producing antagonism within a tryptamine-based series. An electron deficient indole ring system appears essential in order to achieve antagonism, and this is achieved by the inclusion of electron-withdrawing groups at the 2-position of the indole ring. The molecule displacement within the receptor resulting from the inclusion of the bulky 2-substituents also enhances antagonism as this results in the removal of the Π electon density of the indole ring from the region of the receptor normally occupied by the indole ring of 5HT. There also appears to be a structural requirement on the side chain incorporating the protonatable nitrogen, and this is achieved by the inclusion of the bulky 2-ester group which neighbors the 3-ethylamine side chain.

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.

Indolyl tetrahydropyridines for treating migraine

STR1 The present invention is concerned with compounds of formula (I), wherein n is an integer of from 0 to 3: W is a group of formula (i), (ii), or (iii), wherein R is hydrogen or C1-4 alkyl, X is --O--, --S--, --NH--, or --CH2 --, Y is oxygen or sulphur and the chiral center (*) in formula (i) or (ii) is in its (S) or (R) form or is a mixture thereof in any proportions: and Z is a group of formula (iv), (v), or (vi), wherein R1 and R2 are independently selected from hydrogen and C1-4 alkyl and R3 is hydrogen or C1-4 alkyl; and their salts, solvates and physiologically functional derivatives, with processes for their preparation, with medicaments containing them and with their use as therapeutic agents, particularly in the prophylaxis and treatment of migraine.