rel-(4R*,5R*)-4,5-Diphenyloxazolidine-2-one

Base Information

• Chemical Name: rel-(4R*,5R*)-4,5-Diphenyloxazolidine-2-one
• CAS No.: 19190-95-5
• Molecular Formula: C₁₅H₁₃NO₂
• Molecular Weight: 239.274
• Mol file: 19190-95-5.mol

Synonyms:4r,5t-diphenyl-oxazolidin-2-one;trans-4,5-Diphenyl-oxazolidon-2;

Chemical Property of rel-(4R*,5R*)-4,5-Diphenyloxazolidine-2-one

Chemical Property:

• PSA: 38.33000
• LogP: 3.53760

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of rel-(4R*,5R*)-4,5-Diphenyloxazolidine-2-one

There total 21 articles about rel-(4R*,5R*)-4,5-Diphenyloxazolidine-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: 73.0%

4-((rel-(4R,5R)-2-oxo-4,5-diphenyloxazolidin-3-yl)sulfonyl)benzonitrile → rel-(4R,5R)-4,5-diphenyloxazolidin-2-one (19190-95-5,19202-66-5,23204-70-8,23204-71-9,86286-49-9,86286-50-2,92552-75-5)

Guidance literature:

With 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-dodecylthiol; In N,N-dimethyl-formamide; at 20 ℃; for 5h; Inert atmosphere;

DOI:10.1021/acs.orglett.0c00253

Reference yield: 43.0%

isocyanate de chlorosulfonyle (1189-71-5) + trans-Stilbene oxide (1439-07-2) → (4R,5R)-4,5-diphenyl-1,3-dioxolan-2-one (19456-17-8,27797-53-1,28521-60-0,68114-27-2) + rel-(4R,5R)-4,5-diphenyloxazolidin-2-one (19190-95-5,19202-66-5,23204-70-8,23204-71-9,86286-49-9,86286-50-2,92552-75-5)

Guidance literature:

isocyanate de chlorosulfonyle; trans-Stilbene oxide; In dichloromethane; at 0 - 20 ℃; for 1h;

With water; In dichloromethane; for 0.5h;

DOI:10.3762/BJOC.16.148

Reference yield: 24.0%

2-amino-1,2-diphenylethanol (530-36-9,3764-63-4,13286-63-0,23190-16-1,23190-17-2,23364-44-5,23412-95-5,39664-87-4,88082-66-0) + bis(trichloromethyl) carbonate (32315-10-9) → rel-(4R,5R)-4,5-diphenyloxazolidin-2-one (19190-95-5,19202-66-5,23204-70-8,23204-71-9,86286-49-9,86286-50-2,92552-75-5) + cis-4,5-diphenyl-1,3-oxazolidin-2-one (86286-49-9)

Guidance literature:

With pyridine; In dichloromethane; at -78 ℃; for 4h;

upstream raw materials:

(1RS,2SR)-2-chloro-1,2-diphenyl-ethylamine; hydrochloride

sodium carbonate

isocyanate de chlorosulfonyle

trans-Stilbene oxide

Downstream raw materials:

3-amino-4r,5t-diphenyl-oxazolidin-2-one

3-nitroso-4r,5t-diphenyl-oxazolidin-2-one

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

(4R,5R)-trans-4,5-diphenyl-2-oxazolidinone

Refernces

• 1、 Curle, Jonathan M.,Perieteanu, Marina C.,Humphreys, Philip G.,Kennedy, Alan R.,Tomkinson, Nicholas C. O.. "Alkene Syn- And Anti-Oxyamination with Malonoyl Peroxides". . p. 1659 - 1664. Retrieved 2020/02/13.
• 2、 Mattson, Anita E.,Scheidt, Karl A.. "Catalytic additions of acylsilanes to imines: An acyl anion strategy for the direct synthesis of α-amino ketones". . p. 4363 - 4366. Retrieved 2007/10/03.