(5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one
• CAS No.: 380380-56-3
• Molecular Formula: C10H11FN2O2
• Molecular Weight: 210.208
• DSSTox Substance ID: DTXSID401204085
• Mol file: 380380-56-3.mol

Synonyms:(5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one;380380-56-3;SCHEMBL2896939;JUPGGIVRZWNEBD-VIFPVBQESA-N;DTXSID401204085;(5S)-5-(Aminomethyl)-3-(3-fluorophenyl)-2-oxazolidinone;(5S)-5-aminomethyl-3-(3-fluoro-phenyl)-oxazolidin-2-one

Chemical Property of (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one

Chemical Property:

• PSA: 55.56000
• LogP: 1.87490
• XLogP3: 0.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 210.08045576
• Heavy Atom Count: 15
• Complexity: 250

Purity/Quality:

97% ^*data from raw suppliers

(S)-5-(AMINOMETHYL)-3-(3-FLUOROPHENYL)OXAZOLIDIN-2-ONE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: C1C(OC(=O)N1C2=CC(=CC=C2)F)CN
• Isomeric SMILES: C1[C@@H](OC(=O)N1C2=CC(=CC=C2)F)CN

Technology Process of (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one

There total 7 articles about (5S)-5-(aminomethyl)-3-(3-fluorophenyl)-1,3-oxazolidin-2-one 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: 85.0%

(S)-5-(((4-chlorobenzylidene)amino)methyl)-3-(3-fluorophenyl)oxazolidin-2-one → (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one (380380-56-3)

Guidance literature:

With isobutylamine; In toluene; at 83 ℃; for 14h; Inert atmosphere;

DOI:10.1016/j.ejmech.2020.113002

Reference yield:

(R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide (149524-44-7) → (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one (380380-56-3)

Guidance literature:

Reference yield:

meta-fluoroaniline (372-19-0) → (S)-5-(aminomethyl)-3-(3-fluorophenyl)oxazolidin-2-one (380380-56-3)

Guidance literature:

Multi-step reaction with 5 steps

1: sodium hydrogencarbonate / water; acetone / 0 °C

2: n-butyllithium / tetrahydrofuran / -78 - 20 °C

3: triethylamine / dichloromethane

4: sodium azide / N,N-dimethyl-formamide / 70 °C

5: triphenylphosphine / tetrahydrofuran; water / 50 °C

With n-butyllithium; sodium azide; sodium hydrogencarbonate; triethylamine; triphenylphosphine; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone;

DOI:10.1016/j.bmcl.2011.07.034

upstream raw materials:

(R)-[3-(3-fluorophenyl)-2-oxo-5-oxazolidinyl]methyl azide

[(5R)-3-(3-fluorophenyl)-2-oxo-1,3-oxazolidin-5-yl]methyl methanesulfonate

meta-fluoroaniline

3-fluoro-1-nitrobenzene

Downstream raw materials:

(5R)-3-(3-fluorophenyl)-5-[(4-methyl-1H-1,2,3-triazol-1-yl)methyl]-1,3-oxazolidin-2-one

C₂₇H₃₂FN₃O₇

C₁₅H₁₇FN₂O₅

C₂₃H₁₈F₂N₆O₃