(4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one

Base Information

• Chemical Name: (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one
• CAS No.: 1383959-11-2
• Molecular Formula: C₂₅H₂₁NO₄
• Molecular Weight: 399.446
• Mol file: 1383959-11-2.mol

Synonyms:(4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one

Chemical Property of (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one

There total 2 articles about (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-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: 95.0%

(4R)-phenyl-2-oxazolidinone (90319-52-1,7480-32-2) + m-benzyloxy cinnamoyl chloride → (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one (1383959-11-2)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 0 ℃; for 8h; Reagent/catalyst; Temperature; Time; Solvent;

Reference yield:

3-<3-(phenylmethoxy)phenyl>-2-propenoic acid (122024-75-3,138835-16-2) → (4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one (1383959-11-2)

Guidance literature:

Multi-step reaction with 2 steps

1: thionyl chloride / 1 h / Reflux

2: dmap; triethylamine / dichloromethane / 8 h / 0 °C

With dmap; thionyl chloride; triethylamine; In dichloromethane;

Reference yield: 88.0%

(4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one (1383959-11-2) + ethylmagnesium bromide (925-90-6) → (4R)-3-[(3R)-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4-phenyl-2-oxazolidinone (1383959-12-3)

Guidance literature:

ethylmagnesium bromide; With copper(I) bromide dimethylsulfide complex; In tetrahydrofuran; at -40 ℃; for 0.416667h; Inert atmosphere; Large scale reaction;

With boron trifluoride diethyl etherate; In tetrahydrofuran; at -40 ℃; for 0.416667h; Inert atmosphere; Large scale reaction;

(4R)-3-[(2E)-3-[3-(benzyloxy)phenyl]acryloyl]-4-phenyl-oxazolidin-2-one; In tetrahydrofuran; at -40 - -20 ℃; for 2h; diastereoselective reaction; Inert atmosphere; Large scale reaction;

DOI:10.1016/j.tetasy.2012.03.012

upstream raw materials:

(4R)-phenyl-2-oxazolidinone

3-<3-(phenylmethoxy)phenyl>-2-propenoic acid

Downstream raw materials:

tapentadol hydrochloride

(4R)-3-[(2R,3R)-2-methyl-1-oxo-3-[3-(phenylmethoxy)phenyl]pentyl]-4-phenyl-2-oxazolidinone

(R)-3-((2S,3R)-3-[3-(benzyloxy)phenyl]-2-methylpentanoyl)-4-phenyloxazolidin-2-one

(αR,βR)-β-ethyl-α-methyl-3-(phenylmethoxy) benzenepropanoic acid