(4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Base Information

• Chemical Name: (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone
• CAS No.: 17097-67-5
• Molecular Formula: C10H11 N O2
• Molecular Weight: 177.203
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70454975
• Nikkaji Number: J240.059F
• Wikidata: Q82276792
• Mol file: 17097-67-5.mol

Synonyms:17097-67-5;(4S,5S)-4-METHYL-5-PHENYL-2-OXAZOLIDINONE;(4S,5S)-4-methyl-5-phenyloxazolidin-2-one;(4S,5S)-4-methyl-5-phenyl-1,3-oxazolidin-2-one;SCHEMBL5544656;DTXSID70454975;PPIBJOQGAJBQDF-IONNQARKSA-N;AKOS027447683;4beta-Methyl-5alpha-phenyloxazolidine-2-one;((4S,5S)-4-methyl-5-phenyl-2-oxazolidinone;(4S,5S)-4-methyl-5-phenyl-oxazolidin-2-one;(4S,5S)-(+)-4-Methyl-5-phenyl-2-oxazolidinone

Chemical Property of (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone

Chemical Property:

• PSA: 38.33000
• LogP: 2.18480
• Storage Temp.: Refrigerator
• Solubility.: Chloroform (Slightly), DMSO (Slightly), Methanol (Slightly)
• 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:

99%min ^*data from raw suppliers

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

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

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: Intermediate in the preparation of pseudonorephedrine oxazolidinone derivatives

Technology Process of (4S,5S)-4-Methyl-5-phenyl-2-oxazolidinone

There total 64 articles about (4S,5S)-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:

acetophenone semicarbazone

(1S,2S)-2-amino-1-phenylpropanol

(1R,2S)-1-phenyl-2-benzyloxycarbonylamino-1-propanol

tert-butyl ((1R,2S)-1-hydroxy-1-phenylpropan-2-yl)carbamate

Downstream raw materials:

(4S,5R)-4-methyl-5-phenyl-3-propionyloxazolidin-2-one

(4S,5R)-3-(diethoxymethyl)-4-imethyl-5-phenyloxazolidin-2-one

N,N'-bis-((S)-1-methyl-2-phenyl-ethyl)-oxalamide

(4S,5R)-3-(3-Furan-2-yl-propionyl)-4-methyl-5-phenyl-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.