3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone

Base Information

• Chemical Name: 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone
• CAS No.: 198711-59-0
• Molecular Formula: C₂₂H₂₄N₄O₄
• Molecular Weight: 408.457
• Mol file: 198711-59-0.mol

Synonyms:3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone

Chemical Property of 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone

There total 6 articles about 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-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: 87.3%

3(2'S,3'S),4(S)-3-[2'-bromo-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone (198014-53-8) → 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone (198711-59-0)

Guidance literature:

With tetramethylguanidinum azide; In acetonitrile; for 12h; Ambient temperature;

DOI:10.1016/S0957-4166(97)00381-9

Reference yield:

(2E)-4-methylpent-2-enoic acid (1775-44-6,10321-71-8,16666-43-6) → 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone (198711-59-0)

Guidance literature:

Multi-step reaction with 5 steps

1: Et₃N / tetrahydrofuran / 1.25 h / -78 - 0 °C

2: tetrahydrofuran / 3 h / -78 - 20 °C

3: 85.8 percent / CuBr*Me₂S / tetrahydrofuran / 3.25 h / -78 - 20 °C

4: 1.) DIEA, (n-Bu)2BOTf, 2.) NBS / 1.) CH₂Cl₂, from -78 to 0 deg C, 1.25 h, 2.) CH₂Cl₂, from -78 to 0 deg C, 4 h

5: 87.3 percent / tetramethylguanidine azide / acetonitrile / 12 h / Ambient temperature

With N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; triethylamine; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0957-4166(97)00381-9

Reference yield:

4-methoxyphenyl magnesium bromide (13139-86-1) → 3(2'R,3'S),4(S)-3-[2'-azido-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone (198711-59-0)

Guidance literature:

Multi-step reaction with 3 steps

1: 85.8 percent / CuBr*Me₂S / tetrahydrofuran / 3.25 h / -78 - 20 °C

2: 1.) DIEA, (n-Bu)2BOTf, 2.) NBS / 1.) CH₂Cl₂, from -78 to 0 deg C, 1.25 h, 2.) CH₂Cl₂, from -78 to 0 deg C, 4 h

3: 87.3 percent / tetramethylguanidine azide / acetonitrile / 12 h / Ambient temperature

With N-Bromosuccinimide; copper(I) bromide dimethylsulfide complex; di-n-butylboryl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine; tetramethylguanidinum azide; In tetrahydrofuran; acetonitrile;

DOI:10.1016/S0957-4166(97)00381-9

upstream raw materials:

3(2'S,3'S),4(S)-3-[2'-bromo-3'-(4''-methoxyphenyl)-4'-methyl-1'-oxo-2'-pentanyl]-4-phenyl-2-oxazolidinone

(2E)-4-methylpent-2-enoic acid

4-methoxyphenyl magnesium bromide

N-(4'-methyl-2'-pentenoyl)-4S-phenyl-1,3-oxazolidin-2-one

Downstream raw materials:

(2R,3S)-2-azido-3-(4'-methoxyphenyl)-4-methylpentanoic acid