(4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Base Information

• Chemical Name: (4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE
• CAS No.: 16251-45-9
• Molecular Formula: C₁₀H₁₁NO₂
• Molecular Weight: 177.203
• Hs Code.: 29269090
• European Community (EC) Number: 846-836-7
• UNII: PZO2G7843G,4KSX5DI61K
• DSSTox Substance ID: DTXSID10936705,DTXSID40864668
• Nikkaji Number: J411.517A
• Wikidata: Q72495076
• Mol file: 16251-45-9.mol

Synonyms:2-Oxazolidinone,4-methyl-5-phenyl-, (4S,5R)-(-)- (8CI);2-Oxazolidinone, 4-methyl-5-phenyl-,(4S-cis)-;(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone;(4S,5R)-4-Methyl-5-phenyl-2-oxazolidinone;

Chemical Property of (4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

Chemical Property:

• Appearance/Colour: White crystals
• Vapor Pressure: 1.79E-06mmHg at 25°C
• Melting Point: 121-123 °C(lit.)
• Refractive Index: 1.526
• Boiling Point: 395.8 °C at 760 mmHg
• PKA: 12.35±0.60(Predicted)
• Flash Point: 193.2 °C
• PSA: 38.33000
• Density: 1.132 g/cm³
• LogP: 2.18480
• Storage Temp.: Sealed in dry,Room Temperature
• XLogP3: 1.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 1
• Exact Mass: 177.078978594
• Heavy Atom Count: 13
• Complexity: 199

Purity/Quality:

98%, ^*data from raw suppliers

(4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone ^*data from reagent suppliers

Safty Information:

• Safety Statements: 24/25-25-24

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CC1C(OC(=O)N1)C2=CC=CC=C2
• Isomeric SMILES: C[C@H]1[C@H](OC(=O)N1)C2=CC=CC=C2
• Uses: (4S,5R)-(-)-4-Methyl-5-phenyl-2-oxazolidinone may be used to synthesize (4S,5R)-N-tert-butyloxycarbonyl)-4-methyl-5-carboxy-2-oxazolidinone and (+)-pumiliotoxin B.

Technology Process of (4S,5R)-(-)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE

There total 54 articles about (4S,5R)-(-)-4-METHYL-5-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: 99.0%

(-)-(4S,5R,2'S,3'R)-3-(3-hydroxy-2-methylbutanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one (161755-20-0) + ethanethiol (75-08-1) → (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7) + (+)-S-ethyl (2S,3R)-3-hydroxy-2-methylbutanethioate (213319-90-5)

Guidance literature:

With n-butyllithium; In tetrahydrofuran; hexane; at -78 ℃; for 0.5h;

DOI:10.1021/jo9805246

Reference yield: 96.0%

(4S,5R)-3-((2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoyl)-4-methyl-5-phenyl-oxazolidin-2-one (179944-89-9) → (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7) + (2S,3R,4R)-5-Benzyloxy-3-hydroxy-2,4-dimethyl-pentanoic acid methoxy-methyl-amide (179944-90-2)

Guidance literature:

With trimethylaluminum; N,O-dimethylhydroxylamine*hydrochloride; In tetrahydrofuran; dichloromethane; toluene; at -10 - 0 ℃;

DOI:10.1021/jo9606113

Reference yield: 93.0%

(1R,2S)-norephedrine (492-41-1,58550-13-3,757124-50-8) + trichloromethyl chloroformate (503-38-8) → (4S,5R)-4-methyl-5-phenyl-oxazolidin-2-one (16251-45-9,17097-67-5,28044-22-6,28044-23-7,39663-75-7,54418-69-8,77943-39-6,125133-96-2,149055-02-7)

Guidance literature:

With pyrographite; In tetrahydrofuran; at 20 ℃; for 16h;

DOI:10.1055/s-2006-926340

upstream raw materials:

(2RS,3SR)-3-hydroxy-2-methyl-3-phenyl-propionic acid hydrazide

norepinephrine

Diethyl carbonate

sodium carbonate

Downstream raw materials:

4r-methyl-3-nitroso-5t-phenyl-oxazolidin-2-one

norephedrine

(4S,5R)-3-(5-bromovaleryl)-4-methyl-5-phenyl-2-oxazolidinone

(4S,5R)-3-(3-Carboxypropanoyl)-4-methyl-5-phenyl-1,3-oxazolidin-2-one

Refernces

• 1、 Cheng, Jiang-Tao,Dong, Xiao-Yang,Gu, Qiang-Shuai,Li, Zhong-Liang,Liu, Juan,Liu, Xin-Yuan,Luan, Cheng,Wang, Fu-Li,Wang, Li-Lei,Yang, Ning-Yuan,Zhang, Yu-Feng. "Enantioconvergent Cu-Catalyzed Radical C-N Coupling of Racemic Secondary Alkyl Halides to Access α-Chiral Primary Amines". . p. 15413 - 15419. Retrieved 2021/09/30.
• 2、 Reed, Nicholas L.,Herman, Madeline I.,Miltchev, Vladimir P.,Yoon, Tehshik P.. "Tandem copper and photoredox catalysis in photocatalytic alkene difunctionalization reactions". supporting information. p. 351 - 356. Retrieved 2019/02/20.