(3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one

Base Information

• Chemical Name: (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one
• CAS No.: 184784-33-6
• Molecular Formula: C₂₂H₂₅NO₄
• Molecular Weight: 367.445
• Mol file: 184784-33-6.mol

Synonyms:(3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one

Chemical Property of (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one

There total 5 articles about (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-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: 97.0%

4-methoxyphenyl magnesium bromide (13139-86-1) + N-(4'-methyl-2'-pentenoyl)-4S-phenyl-1,3-oxazolidin-2-one (184784-56-3) → (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one (184784-33-6)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; -15 deg C, 2 h; to rt, 1 h;

DOI:10.1016/0040-4039(96)01795-9

Reference yield: 68.0%

1-bromo-4-methoxy-benzene (104-92-7) + N-(4'-methyl-2'-pentenoyl)-4S-phenyl-1,3-oxazolidin-2-one (184784-56-3) → (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one (184784-33-6)

Guidance literature:

With copper(I) bromide dimethylsulfide complex; iodine; magnesium; In tetrahydrofuran; at -15 - 20 ℃; Inert atmosphere;

DOI:10.1021/jo202499j

Reference yield:

(2E)-4-methylpent-2-enoic acid (1775-44-6,10321-71-8,16666-43-6) → (3'S,4S)-3-[3'-(4''-methoxyphenyl)-4'-methylpentanoyl]-4-phenyloxazolidin-2-one (184784-33-6)

Guidance literature:

Multi-step reaction with 3 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

With copper(I) bromide dimethylsulfide complex; triethylamine; In tetrahydrofuran;

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

upstream raw materials:

4-methoxyphenyl magnesium bromide

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

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

1-bromo-4-methoxy-benzene

Downstream raw materials:

(3S)-3-(4'-methoxyphenyl)-4-methylpentanoic acid

(5S)-2-diazo-5-(4'-methoxyphenyl)-6-methylheptan-3-one

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

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