(4S,5R)-4,5-Dimethyl-1,3-oxazolidin-2-one

Base Information

• Chemical Name: (4S,5R)-4,5-Dimethyl-1,3-oxazolidin-2-one
• CAS No.: 19190-97-7
• Molecular Formula: C5H9NO2
• DSSTox Substance ID: DTXSID00565588
• Wikidata: Q82450771
• Mol file: 19190-97-7.mol

Synonyms:(4S,5R)-4,5-Dimethyl-1,3-oxazolidin-2-one;19190-97-7;SCHEMBL10110368;DTXSID00565588;AKOS006354672

Chemical Property of (4S,5R)-4,5-Dimethyl-1,3-oxazolidin-2-one

Chemical Property:

• XLogP3: 0.6
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 0
• Exact Mass: 115.063328530
• Heavy Atom Count: 8
• Complexity: 113

Purity/Quality:

99.90% ^*data from raw suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1C(OC(=O)N1)C
• Isomeric SMILES: C[C@H]1[C@H](OC(=O)N1)C

Technology Process of (4S,5R)-4,5-Dimethyl-1,3-oxazolidin-2-one

There total 10 articles about (4S,5R)-4,5-Dimethyl-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: 77.0%

carbamic acid phenyl ester (622-46-8) + 2,3-trans-epoxybutane (21490-63-1) → 4r,5t-dimethyl-oxazolidin-2-one (19190-96-6,19190-97-7,58628-98-1,87782-30-7)

Guidance literature:

With C₂₅H₂₀AlCl₆NO₄; In acetonitrile; at 50 ℃; for 18h; regioselective reaction;

DOI:10.1002/adsc.201500635

Reference yield: 72.0%

carbamic acid phenyl ester (622-46-8) + 2,3-cis-epoxybutane (925669-95-0) → cis-4.5-dimethyloxazolidin-2-one (19190-96-6,19190-97-7,58628-98-1,87782-30-7)

Guidance literature:

With C₂₅H₂₀AlCl₆NO₄; In acetonitrile; at 50 ℃; for 66h; regioselective reaction;

DOI:10.1002/adsc.201500635

Reference yield:

C10H19NOS → cis-4.5-dimethyloxazolidin-2-one (19190-96-6,19190-97-7,58628-98-1,87782-30-7)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) Br(coll)2ClO₄, 2.) Na₂CO₃ / 1.) CH₂Cl₂, -78 deg C, 30 - 45 min, 2.) H₂O, 25 deg C, 10 h

2: trifluoroacetic acid / 25 °C

3: n-Bu₃SnH

With bromonium bis(collidine) perchlorate; tri-n-butyl-tin hydride; sodium carbonate; In trifluoroacetic acid;

DOI:10.1021/ja00361a053

upstream raw materials:

sodium carbonate

(1RS,2SR)-2-chloro-1-methyl-propylamine; hydrochloride

carbamic acid phenyl ester

2,3-trans-epoxybutane