(4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 128707-87-9
• Molecular Formula: C₂₀H₂₀N₄O₃
• Molecular Weight: 364.404
• Mol file: 128707-87-9.mol

Synonyms:(4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

There total 11 articles about (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-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: 74.0%

(4S)-3-[(2S,3S)-2-bromo-1-oxo-3-phenylbutyl]-4-phenylmethyl-2-oxazolidinon → (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone (128707-87-9)

Guidance literature:

With tetramethylguanidinium azide; sodium hydrogencarbonate; In dichloromethane;

Reference yield:

C15H20O3 (128677-86-1) → (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone (128707-87-9)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) n-BuLi / 1.) THF, hexane, -78 deg C, 20 min, 2a.) THF, 0 deg C, 1 h, 2b.) up to 23 deg C in 16 h

2: 1.) n-Bu₂BOTf, diisopropylethylamine, 2.) NBS / 1.) CH₂Cl₂, 0 deg C, 1 h, 2.) CH₂Cl₂, -78 deg C, 2 h

3: tetramethylguanidinium azide / CH₂Cl₂ / 16 h / Ambient temperature

With N-Bromosuccinimide; n-butyllithium; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; In dichloromethane;

DOI:10.1016/S0040-4020(01)81570-2

Reference yield:

(S)-4-Benzyl-3-((2R,3S)-2-bromo-3-phenyl-butyryl)-oxazolidin-2-one (143251-56-3) → (4S)-3-(2'R,3'S)-2'-azido-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone (128707-87-9)

Guidance literature:

With tetramethylguanidinum azide; In dichloromethane; for 16h; Yield given; Ambient temperature;

DOI:10.1016/S0040-4020(01)81570-2

upstream raw materials:

(4S)-N-[(3R)-phenylbutanoyl]-4-phenylmethyl-1,3-oxazolidin-2-one

(4R)-3-(3'R)-3'-(phenylbutanoyl)-4-(phenylmethyl)-2-oxazolidinone

(S)-4-Benzyl-3-((2R,3S)-2-bromo-3-phenyl-butyryl)-oxazolidin-2-one

(R)-3-phenylbutyric acid

Downstream raw materials:

(2R)-azido-(3S)-phenylbutanoic acid

threo-D-(2R,3S)-β-methylphenylalanine