(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Base Information

• Chemical Name: (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone
• CAS No.: 136620-80-9
• Molecular Formula: C₁₉H₁₈BrNO₄
• Molecular Weight: 404.26
• Mol file: 136620-80-9.mol

Synonyms:(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property of (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone

There total 1 articles about (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-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:

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone (110905-24-3) + benzaldehyde (100-52-7) → (4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-80-9)

Guidance literature:

With triethylamine; Yield given. Multistep reaction;

DOI:10.1021/jo00038a048

Reference yield: 80.0%

(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-80-9) → (4R)-3-((2'S,3'S)-2'-azido-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-81-0)

Guidance literature:

With sodium azide; In dimethyl sulfoxide; for 5h; Ambient temperature;

DOI:10.1021/jo00038a048

Reference yield:

(4R)-3-((2'R,3'S)-2'-bromo-3'-hydroxy-3'-phenylpropanoyl)-4-(phenylmethyl)-2-oxazolidinone (136620-80-9) → (4S,5R)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid methyl ester (141394-65-2)

Guidance literature:

Multi-step reaction with 5 steps

1: 80 percent / NaN₃ / dimethylsulfoxide / 5 h / Ambient temperature

2: 88 percent / CH₂Cl₂; diethyl ether; methanol / 0.05 h / 0 °C

3: 98 percent / H₂ / 10percent Pd-C / ethyl acetate / 2 h / Ambient temperature

4: NEt₃ / CH₂Cl₂ / 0.33 h / 0 °C

5: 12 percent / dimethylformamide / 20 h / Ambient temperature

With sodium azide; hydrogen; triethylamine; palladium on activated charcoal; In methanol; diethyl ether; dichloromethane; dimethyl sulfoxide; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jo00038a048

upstream raw materials:

(4R)-3-(bromoacetyl)-4-(phenylmethyl)-2-oxazolidinone

benzaldehyde

Downstream raw materials:

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

(2S,3S)-2-azido-3-phenyl-3-hydroxypropionic acid methyl ester

(4S,5R)-2-Oxo-5-phenyl-oxazolidine-4-carboxylic acid methyl ester

(2R,3R)-2-((tert-butyloxycarbonyl)amino)-3-((4-methylbenzyl)thio)-3-phenylpropionic acid