(3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 113543-41-2
• Molecular Formula: C₁₉H₁₈N₄O₃
• Molecular Weight: 350.377
• Mol file: 113543-41-2.mol

Synonyms:(3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone

There total 6 articles about (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-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: 91.0%

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (113543-41-2) + (3(2S),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (111525-66-7)

Guidance literature:

With p-nitrobenzenesulfonyl azide; potassium hexamethylsilazane; acetic acid; In tetrahydrofuran; toluene; Product distribution; Mechanism; other carboximides and reagents;

Reference yield:

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one (136159-65-4,96930-27-7) → (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (113543-41-2)

Guidance literature:

Multi-step reaction with 2 steps

1: 1.) Bu₂BOTf, R₃N, 2.) NBS / 2.) CH₂Cl₂, -78 deg C, 75 min.

2: tetramethylguanidinium azide / CH₂Cl₂ / 3 h / 0 °C / var.: NaN₃, DMF or DMSO, 0 deg C

With N-Bromosuccinimide; di-n-butylboryl trifluoromethanesulfonate; tetramethylguanidinum azide; In dichloromethane;

DOI:10.1016/S0040-4039(00)95305-X

Reference yield:

(4S)-3-(2-bromo-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (113543-31-0,113543-32-1) → (3(2R),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (113543-41-2) + (3(2S),4S)-3-(2-azido-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone (111525-66-7)

Guidance literature:

With tetramethylguanidinum azide; In dichloromethane; Yield given; 1.) 0 deg C, 0.5 h, 2.) 25 deg C, 1.0 h;

upstream raw materials:

(S)-4-benzyl-3-(3-phenylpropanoyl)oxazolidin-2-one

(4S)-3-(2-bromo-3-phenyl-1-oxopropyl)-4-(phenylmethyl)-2-oxazolidinone

(S)-4-Benzyl-3-((S)-2-bromo-3-phenyl-propionyl)-oxazolidin-2-one

(S)-4-Benzyl-2-oxazolidinone

Downstream raw materials:

(R)-2-azido-3-phenylpropionic acid

D-(R)-phenylalanine