(S)-4-(4-Nitrobenzyl)-2-oxazolidinone

Base Information

• Chemical Name: (S)-4-(4-Nitrobenzyl)-2-oxazolidinone
• CAS No.: 139264-55-4
• Molecular Formula: C10H10N2O4
• Molecular Weight: 222.2
• Mol file: 139264-55-4.mol

Synonyms:2-Oxazolidinone,4-[(4-nitrophenyl)methyl]-, (S)-;

Chemical Property of (S)-4-(4-Nitrobenzyl)-2-oxazolidinone

Chemical Property:

• Boiling Point: 509.509 °C at 760 mmHg
• PKA: 12.24±0.40(Predicted)
• Flash Point: 261.942 °C
• PSA: 84.15000
• Density: 1.368g/cm³
• LogP: 2.09770
• Storage Temp.: 2-8°C

Purity/Quality:

99% ^*data from raw suppliers

(4S)-4-[(4-Nitrophenyl)methyl]-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Uses: (4S)-4-[(4-Nitrophenyl)methyl]-2-oxazolidinone is an impurity in the synthesis of 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan-d6 3-Acetic Acid (D288969) which is the isotope labelled 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan 3-Acetic Acid (D288965). 3-Des[2-(Dimethylamino)ethyl] Zolmitriptan 3-Acetic Acid is the indole acetic acid metabolite of Zolmitriptan (Z639000) formed by human hepatocytes.

Technology Process of (S)-4-(4-Nitrobenzyl)-2-oxazolidinone

There total 9 articles about (S)-4-(4-Nitrobenzyl)-2-oxazolidinone which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 87.0%

(S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol (89288-22-2,174302-89-7) + Diethyl carbonate (105-58-8,76619-83-5) → (S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one (139264-55-4)

Guidance literature:

With potassium carbonate; In ethanol; at 130 - 135 ℃; for 1h;

DOI:10.1039/c4ob00448e

Reference yield: 75.0%

phosgene (75-44-5) + (S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol (89288-22-2,174302-89-7) → (S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one (139264-55-4)

Guidance literature:

With potassium hydroxide; In toluene; at 0 - 20 ℃; for 2h;

DOI:10.1021/jm9605849

Reference yield: 65.0%

(S)-4-Benzyl-2-oxazolidinone (90719-32-7) → (S)-4-(4'-nitrobenzyl)-1,3-oxazolidin-2-one (139264-55-4)

Guidance literature:

With nitric acid; In dichloromethane; at 20 ℃; for 2h;

DOI:10.1016/S0045-2068(02)00017-2

upstream raw materials:

phosgene

(S)-(-)-2-amino-3-(4-nitrophenyl)propan-1-ol

(S)-4-Benzyl-2-oxazolidinone

bis(trichloromethyl) carbonate

Downstream raw materials:

(S)-3-((1S,2R)-1,2-diethyl-2-vinylcyclopropanecarbonyl)-4-(4-nitrobenzyl)oxazolidin-2-one

(S)-3-((1R,2S)-1,2-diethyl-2-vinylcyclopropanecarbonyl)-4-(4-nitrobenzyl)oxazolidin-2-one

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

(S)-2-<5-<(2-oxo-1,3-oxazolidin-4-yl)methyl>-1H-indol-3-yl>ethylamine

Refernces

• 1、 -. "AN IMPROVED PROCESS FOR THE PREPARATION OF ZOLMITRIPTAN". Page/Page column 8. . Retrieved 2008/06/13.
• 2、 Moloney, Gerard P.,Robertson, Alan D.,Martin, Graeme R.,MacLennan, Steven,Mathews, Neil,Dodsworth, Susan,Sang, Pang Yih,Knight, Cameron,Glen, Robert. "A novel series of 2,5-substituted tryptamine derivatives as vascular 5HT(1B/1D) receptor antagonists". . p. 2347 - 2362. Retrieved 2007/10/03.