Acetamide, N-[[(5S)-3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl]-

Base Information

• Chemical Name: Acetamide, N-[[(5S)-3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl]-
• CAS No.: 104392-75-8
• Molecular Formula: C14H14N2O3
• Molecular Weight: 258.277
• Mol file: 104392-75-8.mol

Synonyms:(S)-N-{[3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl}acetamide;N-[(S)-3-(4-Ethynyl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide;

Chemical Property of Acetamide, N-[[(5S)-3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl]-

Chemical Property:

• Melting Point: 169.5-171.5 °C
• Boiling Point: 476.9±28.0 °C(Predicted)
• PSA: 58.64000
• Density: 1.27±0.1 g/cm3(Predicted)
• LogP: 1.58510

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of Acetamide, N-[[(5S)-3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl]-

There total 3 articles about Acetamide, N-[[(5S)-3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl]methyl]- 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: 63.0%

(S)-N-<<3-<4-<2-(trimethylsilyl)ethynyl>phenyl>2-oxo-5-oxazolidinyl>methyl>acetamide (104392-76-9) → (S)-N-<<3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide (104392-75-8)

Guidance literature:

With potassium hydroxide; In methanol; at 25 ℃; for 1.5h;

DOI:10.1021/jm00171a035

Reference yield:

(S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide (96800-17-8) → (S)-N-<<3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide (104392-75-8)

Guidance literature:

Multi-step reaction with 3 steps

1: 24.762 g / I₂, AgOCOCF₃ / CHCl₃; acetonitrile / 18 h

2: 84 percent / bis(triphenylphosphine)palladium(II) chloride, CuI, Et₃N / dimethylformamide / 4.5 h / 45 °C

3: 63 percent / 1 N aq. KOH / methanol / 1.5 h / 25 °C

With potassium hydroxide; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; iodine; silver trifluoroacetate; triethylamine; In methanol; chloroform; N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00171a035

Reference yield:

(S)-N-<<3-(4-iodophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide (104392-74-7) → (S)-N-<<3-(4-ethynylphenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide (104392-75-8)

Guidance literature:

Multi-step reaction with 2 steps

1: 84 percent / bis(triphenylphosphine)palladium(II) chloride, CuI, Et₃N / dimethylformamide / 4.5 h / 45 °C

2: 63 percent / 1 N aq. KOH / methanol / 1.5 h / 25 °C

With potassium hydroxide; copper(l) iodide; bis(triphenylphosphine)palladium(II)-chloride; triethylamine; In methanol; N,N-dimethyl-formamide;

DOI:10.1021/jm00171a035

upstream raw materials:

(S)-N-<<3-<4-<2-(trimethylsilyl)ethynyl>phenyl>2-oxo-5-oxazolidinyl>methyl>acetamide

(S)-N-<<3-phenyl-2-oxo-5-oxazolidinyl>methyl>acetamide

(S)-N-<<3-(4-iodophenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide

Downstream raw materials:

(S)-N-<<3-(4-ethenylphenyl)-2-oxo-5-oxazolidinyl>methyl>acetamide

N-[(S)-3-(4-Ethyl-phenyl)-2-oxo-oxazolidin-5-ylmethyl]-acetamide