(S)-(+)-4-Phenyl-2-oxazolidinone

Base Information

• Chemical Name: (S)-(+)-4-Phenyl-2-oxazolidinone
• CAS No.: 99395-88-7
• Molecular Formula: C9H9NO2
• Molecular Weight: 163.176
• Hs Code.: 29349990
• European Community (EC) Number: 619-429-5
• UNII: DJ3K4V6J29
• DSSTox Substance ID: DTXSID10912726
• Nikkaji Number: J616.889B
• Wikidata: Q72498037
• Mol file: 99395-88-7.mol

Synonyms:99395-88-7;(S)-(+)-4-Phenyl-2-oxazolidinone;(s)-4-phenyl-2-oxazolidinone;(S)-4-Phenyloxazolidin-2-one;(4S)-4-phenyl-1,3-oxazolidin-2-one;2-Oxazolidinone, 4-phenyl-, (4S)-;(4S)-4-phenyloxazolidin-2-one;86217-38-1;(S)-Poz;DJ3K4V6J29;(+)-4-phenyl-2-oxazolidinone;(4S)-4-phenyl-2-oxazolidinone;2-Oxazolidinone, 4-phenyl-, (S)-;MFCD00043396;(S)-4-phenyloxazolidinone;SCHEMBL4562;UNII-DJ3K4V6J29;4beta-Phenyloxazolidine-2-one;(S)-4-phenyloxazoldin-2-one;(S)-4-Phenyl-oxazolidin-2-on;(S)-4-phenyl-oxazolidin-2-one;DTXSID10912726;4-Phenyl-2-oxazolidinone, (4S)-;(s)-(+)-4-phenyloxazolidin-2-one;AKOS005259882;(S)-(+)-4-phenyl-oxazolidin-2-one;AC-8429;CS-M-57852;AS-12030;4-Phenyl-4,5-dihydro-1,3-oxazol-2-ol;(S)-(+)-4-Phenyl-2-oxazolidinone, 98%;AM20060772;CS-0031471;P1308;(4s)-(+)-4-phenyl-1,3-oxazolidin-2-one;EN300-258709;A846016

Chemical Property of (S)-(+)-4-Phenyl-2-oxazolidinone

Chemical Property:

• Appearance/Colour: white crystalline powder
• Vapor Pressure: 7.79E-07mmHg at 25°C
• Melting Point: 129-132 °C(lit.)
• Refractive Index: 72 ° (C=1, AcOEt)
• Boiling Point: 407 °C at 760 mmHg
• PKA: 12.05±0.40(Predicted)
• Flash Point: 200 °C
• PSA: 38.33000
• Density: 1.195 g/cm³
• LogP: 1.79630
• Storage Temp.: Store at 0-5°C
• Solubility.: Chloroform (Slightly), Methanol (Slightly)
• XLogP3: 1.2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 163.063328530
• Heavy Atom Count: 12
• Complexity: 175

Purity/Quality:

99.0% min ^*data from raw suppliers

(S)-4-Phenyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi,F+
• Hazard Codes: Xi,F+
• Statements: 12-36
• Safety Statements: 24/25-33-26-16-7/9

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1C(NC(=O)O1)C2=CC=CC=C2
• Isomeric SMILES: C1[C@@H](NC(=O)O1)C2=CC=CC=C2
• Uses: S)-4-Phenyl-2-oxazolidinone is an intermediate for the synthesis and development for cholesterol absorption inhibitor AZD4121. Ezetimibe intermediate Versatile chiral auxiliary for asymmetric synthesis which is easily recycled under mild conditions, thus enhancing its commercial potential. For a recent review, see Aldrichimica Acta .

Technology Process of (S)-(+)-4-Phenyl-2-oxazolidinone

There total 95 articles about (S)-(+)-4-Phenyl-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: 98.0%

4-phenyl-4-oxazoline-2-one (34375-80-9) → (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2)

Guidance literature:

With (+)-1,2-bis((2S,5S)-2,5-diphenylphospholanyl)ethane; hydrogen; nickel diacetate; In 2,2,2-trifluoroethanol; at 50 ℃; for 12h; under 760.051 Torr; Solvent; Temperature; Pressure; Reagent/catalyst; enantioselective reaction; Catalytic behavior;

DOI:10.1021/acscatal.0c02569

Reference yield: 96.0%

(R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one (148766-15-8) → (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2) + (2S,3S)-3-methylpyroglutamic acid (132435-54-2) + o-[N-(α-picolyl)amino]acetophenone (261768-47-2)

Guidance literature:

(R,E)-3-but-2-enoyl-4-phenyloxazolidin-2-one; Schiff base of glycine with o-[N-α-pycolylamino]acetophenone; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In N,N-dimethyl-formamide; at 20 ℃; for 0.333333h;

With hydrogenchloride; In methanol; at 70 ℃;

With cation-exchange resin Dowex; water;

DOI:10.1021/ol990402f

Reference yield: 95.0%

carbon dioxide (124-38-9,18923-20-1) + (2S)-2-phenylglycinol (20989-17-7) → (S)-4-phenyl-2-oxazolidinone (99395-88-7,7480-32-2)

Guidance literature:

carbon dioxide; (2S)-2-phenylglycinol; With 1,8-diazabicyclo[5.4.0]undec-7-ene; In acetonitrile; at 20 ℃; for 0.75h;

With tributylphosphine; di-tert-butyl-diazodicarboxylate; In acetonitrile; at 0 ℃; for 0.333333h;

DOI:10.1021/ol0491080

upstream raw materials:

4-phenyl-2-oxazolidinone

(S)-2-((ethoxycarbonyl)amino)-2-phenylacetic acid

(2S)-2-phenylglycinol

Diethyl carbonate

Downstream raw materials:

4S-3-(2-bromoacetyl)-4-(phenyl)-2-oxazolidinone

(4S)-3-((2E)-2-butenoyl)-4-phenyl-1,3-oxazolidin-2-one

(4S)-3-((2'R)-2'-methylbutanoyl)-4-phenyl-2-oxazolidinone

(4S)-3-((2'S)-2'-methylbutanoyl)-4-phenyl-2-oxazolidinone

Refernces

A new approach to asymmetric synthesis of β-amino alcohols by means of α-chirally protected amino alkyllithiums

10.1055/s-1998-1891

The research presents a novel and general synthetic approach to the asymmetric synthesis of enantiopure α-amino ketones and syn-β-amino alcohols, which are key components of bio-active molecules. The study employs α-amino alkyllithiums, generated via an improved version of Pearson's transmetalative protocol, as key synthetic intermediates. The purpose of this research was to overcome the challenges associated with the enantioselective generation and configurational instability of α-amino organolithiums, which had limited the exploration of this synthetic route. The researchers successfully developed a more convenient and flexible route to the requisite stannane, and demonstrated the synthetic potential of this method in the context of the asymmetric synthesis of syn-β-amino α-trifluoromethyl alcohol, a candidate for protease inhibitor. The chemicals used in the process include α-hydroxy stannane, potassium salt of (S)-4-phenyl-2-oxazolidinone, n-BuLi, aldehydes, Dess-Martin periodinane, L-Selectride, and benzyloxycarbonyl chloride, among others. The conclusions of the research indicate the development of an efficient and flexible synthetic route to enantiopure α-amino ketones and syn-α-amino alcohols, with ongoing work to expand the synthetic scope of this methodology.