4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester

Base Information

• Chemical Name: 4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester
• CAS No.: 154590-42-8
• Molecular Formula: C₁₉H₂₇FN₄O₄
• Molecular Weight: 394.446
• Mol file: 154590-42-8.mol

Synonyms:4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester;1-Piperazinecarboxylic acid, 4-[4-[5-(aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-, 1,1-dimethylethyl ester

Chemical Property of 4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester

Chemical Property:

• Boiling Point: 542.6 °C at 760 mmHg
• Flash Point: 281.9 °C
• PSA: 88.34000
• Density: 1.268 g/cm³
• LogP: 2.93490

Purity/Quality:

99% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of 4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester

There total 10 articles about 4-[4-[5-(Aminomethyl)-2-oxo-3-oxazolidinyl]-2-fluorophenyl]-1-piperazinecarboxylic acid tert-butyl ester 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: 78.0%

(S)-N-[3-[3-fluoro-4-[N-t-butoxycarbonylpiperazin-1-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]azide (154590-64-4) → tert-butyl 4-(4-((S)-5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate (268209-15-0,154590-42-8)

Guidance literature:

With water; triphenylphosphine; In tetrahydrofuran;

DOI:10.1016/j.bmcl.2008.03.043

Reference yield:

(R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate (154590-62-2) → tert-butyl 4-(4-((S)-5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate (268209-15-0,154590-42-8)

Guidance literature:

(R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate; With methanesulfonyl chloride; triethylamine; In dichloromethane; at 0 - 20 ℃;

With potassium phtalimide; In acetonitrile; at 180 ℃; for 0.75h; microwave irradiation;

With hydrazine hydrate; In methanol; for 2h; Heating;

DOI:10.1021/jm050101d

Reference yield:

(5R)-[3-[3-fluoro-4-[N-t-butoxycarbonylpiperazin-1-yl]phenyl]-2-oxo-5-oxazolidinylmethyl] nosylate (874820-28-7) → tert-butyl 4-(4-((S)-5-(aminomethyl)-2-oxooxazolidin-3-yl)-2-fluorophenyl)piperazine-1-carboxylate (268209-15-0,154590-42-8)

Guidance literature:

With ammonia; In water; acetonitrile; at 40 ℃; Product distribution / selectivity;

upstream raw materials:

(R)-tert-butyl-4-(2-fluoro-4-(5-(hydroxymethyl)-2-oxooxazolidin-3-yl)phenyl)piperazine-1-carboxylate

(S)-N-[3-[3-fluoro-4-[N-t-butoxycarbonylpiperazin-1-yl]phenyl]-2-oxooxazolidin-5-ylmethyl]azide

tert-butyl 4-(4-amino-2-fluorophenyl)piperazine-1-carboxylate

4-(2-fluoro-4-nitrophenyl)-piperazine-1-carboxylic acid tert butyl ester

Refernces

• 1、 Kamal, Ahmed,Swapna,Shetti, Rajesh V.C.R.N.C.,Shaik, Anver Basha,Narasimha Rao,Gupta, Soma. "Synthesis, biological evaluation of new oxazolidino-sulfonamides as potential antimicrobial agents". . p. 661 - 669. Retrieved 2013/05/09.
• 2、 Phillips, Oludotun A.,Udo, Edet E.,Abdel-Hamid, Mohammed E.,Varghese, Reny. "Synthesis and antibacterial activity of novel 5-(4-methyl-1H-1,2,3-triazole) methyl oxazolidinones". experimental part. p. 3217 - 3227. Retrieved 2009/12/04.