(S)-4-Benzyl-5,5-diphenyloxazolidin-2-one

Base Information

• Chemical Name: (S)-4-Benzyl-5,5-diphenyloxazolidin-2-one
• CAS No.: 191090-38-7
• Molecular Formula: C22H19 N O2
• Molecular Weight: 329.398
• Hs Code.: 2934999090
• DSSTox Substance ID: DTXSID70431307
• Nikkaji Number: J2.035.855F
• Wikidata: Q72441148
• Mol file: 191090-38-7.mol

Synonyms:191090-38-7;(S)-4-Benzyl-5,5-diphenyloxazolidin-2-one;(4S)-4-Benzyl-5,5-diphenyl-1,3-oxazolidin-2-one;(S)-(-)-5,5-Diphenyl-4-(phenylmethyl)-2-oxazolidinone;(S)-(-)-5,5-DIPHENYL-4-BENZYL-2-OXZOLIDINONE;2-Oxazolidinone, 5,5-diphenyl-4-(phenylmethyl)-, (4S)-;(S)-4-benzyl-5,5-diphenyl-2-oxazolidinone;SCHEMBL5872462;DTXSID70431307;XVHANMSUSBZRCX-FQEVSTJZSA-N;AMY37566;AKOS015911285;(4S)-4-Benzyl-5,5-diphenyloxazolidine-2-one;A934616;2-Oxazolidinone,5,5-diphenyl-4-(phenylmethyl)-,(4S)-;(S)-(-)-5,5-Diphenyl-4-(phenylmethyl)-2-oxazolidinone, 98%

Chemical Property of (S)-4-Benzyl-5,5-diphenyloxazolidin-2-one

Chemical Property:

• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 250-254 ºC(lit.)
• Boiling Point: 553 ºC at 760 mmHg
• Flash Point: 288.3 ºC
• PSA: 38.33000
• Density: 1.187 g/cm³
• LogP: 4.61010
• XLogP3: 4.8
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 2
• Rotatable Bond Count: 4
• Exact Mass: 329.141578849
• Heavy Atom Count: 25
• Complexity: 427

Purity/Quality:

98.5% ^*data from raw suppliers

(S)-(?)-5,5-Diphenyl-4-(phenylmethyl)-2-oxazolidinone 98% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC=C(C=C1)CC2C(OC(=O)N2)(C3=CC=CC=C3)C4=CC=CC=C4
• Isomeric SMILES: C1=CC=C(C=C1)C[C@H]2C(OC(=O)N2)(C3=CC=CC=C3)C4=CC=CC=C4

Technology Process of (S)-4-Benzyl-5,5-diphenyloxazolidin-2-one

There total 7 articles about (S)-4-Benzyl-5,5-diphenyloxazolidin-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: 66.0%

(S)-3-(2'-benzyl-3'-phenylpropionyl)-4-benzyl-5,5-diphenyloxazolidin-2-one (637330-69-9) → 2-benzyl-3-phenylpropionaldehyde (22859-80-9) + (S)-(-)-5-benzyl-4,4-diphenyl-1,3-oxazolidinone (191090-38-7) + (S)-2-(2'-benzyl-3'-phenylpropionylamino)-2-benzyl-1,1-diphenylethyl formate

Guidance literature:

With diisobutylaluminium hydride; In hexane; dichloromethane; at -78 ℃;

DOI:10.1039/b305623f

Reference yield:

4-benzyl-5,5-diphenyloxazolidin-2-one → (R)-(-)-5,5-diphenyl-4-benzyl-2-oxazolidinone (191090-40-1) + (S)-(-)-5-benzyl-4,4-diphenyl-1,3-oxazolidinone (191090-38-7)

Guidance literature:

With Pirkle-type column (Whelk-O-1 CSP); In hexane; isopropyl alcohol; Reagent/catalyst; Resolution of racemate;

DOI:10.1002/bkcs.10116

Reference yield:

((S)-1-Benzyl-2-hydroxy-2,2-diphenyl-ethyl)-carbamic acid ethyl ester → (S)-(-)-5-benzyl-4,4-diphenyl-1,3-oxazolidinone (191090-38-7)

Guidance literature:

With sodium hydroxide; In methanol; for 9h; Yield given; Heating;

DOI:10.1002/(SICI)1522-2675(19981111)81:11<2093::AID-HLCA2093>3.0.CO;2-X

upstream raw materials:

(S)-(-)-2-amino-1,1,3-triphenyl-1-propanol

trichloromethyl chloroformate

(S)-3-(2'-benzyl-3'-phenylpropionyl)-4-benzyl-5,5-diphenyloxazolidin-2-one

H-Phe-OEt

Downstream raw materials:

(S)-1-Benzyl-2,2-diphenyl-ethylamine

(S)-3-(3'-phenylpropionyl)-4-benzyl-5,5-diphenyloxazolidin-2-one

(S)-3-amino-4-benzyl-5,5-diphenyloxazolidin-2-one

(R)-pentafluorophenyl 2-phenylpropionate