(4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester

Base Information

• Chemical Name: (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester
• CAS No.: 294637-48-2
• Molecular Formula: C₁₉H₁₆N₂O₇
• Molecular Weight: 384.345
• Mol file: 294637-48-2.mol

Synonyms:(4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester

Chemical Property of (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester

There total 2 articles about (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester 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: 62.0%

(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (142917-83-7) + Benzoyl isothiocyanate (532-55-8) → (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester (294637-48-2)

Guidance literature:

(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester; With di(n-butyl)tin oxide; In 1,2-dichloro-ethane; for 24h; Heating;

Benzoyl isothiocyanate; for 6h; Heating;

With tetrabutylammomium bromide; for 6h; Heating;

DOI:10.1016/S0040-4039(00)00878-9

Reference yield:

ethyl (E)-3-(4-nitrophenyl)-2-propenoate (24393-61-1) → (4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester (294637-48-2)

Guidance literature:

Multi-step reaction with 2 steps

1.1: 98 percent / AD-mix-β

2.1: Bu₂SnO / 1,2-dichloro-ethane / 24 h / Heating

2.2: 6 h / Heating

2.3: 62 percent / Bu₄NBr / 6 h / Heating

With AD-mix-β; di(n-butyl)tin oxide; In 1,2-dichloro-ethane; 1.1: Dihydroxylation / 2.1: Stannylation / 2.2: Cyclization / 2.3: Rearrangement;

DOI:10.1016/S0040-4039(00)00878-9

Reference yield: 80.0%

(4S,5R)-3-Benzoyl-5-(4-nitro-phenyl)-2-oxo-oxazolidine-4-carboxylic acid ethyl ester (294637-48-2) → ethyl (4S,5R)-5-(4-nitrophenyl)-2-oxooxazolidine-4-carboxylate (294637-50-6)

Guidance literature:

With titanium(IV) isopropylate; In ethanol;

DOI:10.1016/S0040-4039(00)00878-9

upstream raw materials:

(2S,3R)-2,3-Dihydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester

Benzoyl isothiocyanate

ethyl (E)-3-(4-nitrophenyl)-2-propenoate

Downstream raw materials:

ethyl (4S,5R)-5-(4-nitrophenyl)-2-oxooxazolidine-4-carboxylate

chloramphenicol

(1R,2R)-2-Amino-1-(4-nitrophenyl)-1,3-propanediol

(4R,5R)-5-(4-nitrophenyl)-4-hydroxymethyl-1,3-oxazolidin-2-one