(R)-4-(4-chlorophenyl)oxazolidin-2-one

Base Information

• Chemical Name: (R)-4-(4-chlorophenyl)oxazolidin-2-one
• CAS No.: 1147391-02-3
• Molecular Formula: C9H8ClNO2
• Molecular Weight: 197.621
• Mol file: 1147391-02-3.mol

Synonyms:(R)-4-(4-chlorophenyl)oxazolidin-2-one

Chemical Property of (R)-4-(4-chlorophenyl)oxazolidin-2-one

Chemical Property:

• Boiling Point: 432.0±44.0 °C(Predicted)
• PKA: 11.86±0.40(Predicted)
• PSA: 38.33000
• Density: 1.331±0.06 g/cm3(Predicted)
• LogP: 2.44970

Purity/Quality:

97% ^*data from raw suppliers

(R)-4-(4-chlorophenyl)oxazolidin-2-one ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

Technology Process of (R)-4-(4-chlorophenyl)oxazolidin-2-one

There total 3 articles about (R)-4-(4-chlorophenyl)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: 61.0%

4-vinylbenzyl chloride (1073-67-2,24991-47-7) + sodium isocyanate (917-61-3) → (R)-4-(4-chlorophenyl)oxazolidin-2-one (1147391-02-3)

Guidance literature:

With recombinant strain Escherichia coli constructed by co-expression of a styrene monooxygenase from Pseudomonas sp. VLB₁₂₀ and a glucose dehydrogenase from Bacillus subtilis QB₉₂₈; recombinant strain Escherichia coli constructed by expression of a halohydrin dehalogenase from Ilumatobacter coccineus YM₁₆-304; air; In dimethyl sulfoxide; at 30 ℃; for 12h; pH=8.5; enantioselective reaction; Enzymatic reaction;

DOI:10.1002/adsc.202100468

Reference yield: 33.0%

bis(trichloromethyl) carbonate (32315-10-9) + (R)-2-amino-2-(4-chlorophenyl)acetic acid (43189-37-3,7292-70-8) → (R)-4-(4-chlorophenyl)oxazolidin-2-one (1147391-02-3)

Guidance literature:

(R)-2-amino-2-(4-chlorophenyl)acetic acid; With borane-THF; In tetrahydrofuran; at 0 - 20 ℃;

With methanol; In tetrahydrofuran; for 0.5h;

bis(trichloromethyl) carbonate; With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 0 - 20 ℃;

Reference yield:

C19H20ClNO7 → (R)-4-(4-chlorophenyl)oxazolidin-2-one (1147391-02-3) + (S)-4-(4-chlorophenyl)oxazolidin-2-one (1147391-29-4)

Guidance literature:

With C₄₈H₄₂F₆N₈Ru⁽²⁺⁾*2F₆P^(1-); potassium carbonate; In 1,2-dichloro-benzene; at 40 ℃; for 20h; Overall yield = 92 percent; enantioselective reaction; Inert atmosphere;

DOI:10.1007/s11426-020-9906-x

upstream raw materials:

bis(trichloromethyl) carbonate

(R)-2-amino-2-(4-chlorophenyl)acetic acid

4-vinylbenzyl chloride

sodium isocyanate

Downstream raw materials:

(R)-4-(4-chlorophenyl)-3-isopropyl-oxazolidin-2-one

(R)-4-(4'-(2-((R)-2-methylpyrrolidin-1-yl)ethyl)biphenyl-4-yl)oxazolidin-2-one