(5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one
• CAS No.: 919081-45-1
• Molecular Formula: C12H13NO4
• Molecular Weight: 235.24
• DSSTox Substance ID: DTXSID30582384
• Wikidata: Q82473796
• Mol file: 919081-45-1.mol

Synonyms:919081-45-1;(5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one;DTXSID30582384

Chemical Property of (5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

Chemical Property:

• XLogP3: 0.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 3
• Exact Mass: 235.08445790
• Heavy Atom Count: 17
• Complexity: 318

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(=O)C1=CC(=CC=C1)N2CC(OC2=O)CO
• Isomeric SMILES: CC(=O)C1=CC(=CC=C1)N2C[C@H](OC2=O)CO

Technology Process of (5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-1,3-oxazolidin-2-one

There total 2 articles about (5S)-3-(3-acetylphenyl)-5-(hydroxymethyl)-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:

3-acetylphenylcarbamic acid benzyl ester (42865-67-8) + (S)-glycidyl butyrate (65031-96-1) → (S)-3-(3-acetylphenyl)-5-(hydroxymethyl)oxazolidin-2-one (919081-45-1)

Guidance literature:

3-acetylphenylcarbamic acid benzyl ester; With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.75h;

(S)-glycidyl butyrate; In tetrahydrofuran; hexane; at -78 - 20 ℃;

DOI:10.1021/jm060666p

Reference yield:

1-(3-aminophenyl)ethanone (99-03-6) → (S)-3-(3-acetylphenyl)-5-(hydroxymethyl)oxazolidin-2-one (919081-45-1)

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaHCO₃ / acetone; H₂O / 20 °C

2.1: n-BuLi / tetrahydrofuran; hexane / 0.75 h / -78 °C

2.2: tetrahydrofuran; hexane / -78 - 20 °C

With n-butyllithium; sodium hydrogencarbonate; In tetrahydrofuran; hexane; water; acetone;

DOI:10.1021/jm060666p

Reference yield:

(S)-3-(3-acetylphenyl)-5-(hydroxymethyl)oxazolidin-2-one (919081-45-1) → (S)-3-(3-acetylphenyl)-2-oxo-oxazolidine-5-carboxylic acid (918543-54-1)

Guidance literature:

With sodium periodate; ruthenium trichloride; In tetrachloromethane; acetonitrile; at 0 - 20 ℃;

DOI:10.1021/jm060666p

upstream raw materials:

3-acetylphenylcarbamic acid benzyl ester

(S)-glycidyl butyrate

1-(3-aminophenyl)ethanone

Downstream raw materials:

(S)-3-(3-acetylphenyl)-2-oxo-oxazolidine-5-carboxylic acid

3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carbonyl chloride

3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-methoxy-benzenesulfonyl)-amino]-propyl}-amide

3-(3-acetyl-phenyl)-2-oxo-oxazolidine-5-carboxylic acid {1-benzyl-2-hydroxy-3-[isobutyl-(4-nitro-benzenesulfonyl)-amino]-propyl}-amide