2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester

Base Information

• Chemical Name: 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester
• CAS No.: 19185-38-7
• Molecular Formula: C₁₈H₁₈N₂O₆
• Molecular Weight: 358.351
• Mol file: 19185-38-7.mol

Synonyms:

Chemical Property of 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester

There total 8 articles about 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic 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: 92.0%

3-ethoxy-2-benzamido-3-oxopropanoic acid (84337-81-5) + 4-nitrobenzaldehdye (555-16-8) → 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester (19185-38-7,19185-39-8,101976-78-7)

Guidance literature:

With triethylamine; In tetrahydrofuran; at 25 ℃; for 15h; Solvent; Reagent/catalyst; Temperature; Concentration; diastereoselective reaction; Catalytic behavior;

DOI:10.1021/ol402805f

Reference yield: 38.0%

3-ethoxy-2-benzamido-3-oxopropanoic acid (84337-81-5) + 4-nitrobenzaldehdye (555-16-8) → (Z)-ethyl 2-benzamido-3-(4-nitrophenyl)acrylate (93634-60-7,93913-55-4) + 2-benzoylamino-3-hydroxy-3-(4-nitrophenyl)propionic acid ethyl ester (19185-38-7,19185-39-8,101976-78-7)

Guidance literature:

3-ethoxy-2-benzamido-3-oxopropanoic acid; With triethylamine; In tetrahydrofuran; Inert atmosphere; Molecular sieve;

4-nitrobenzaldehdye; With pyrrolidine; trifluorormethanesulfonic acid; In tetrahydrofuran; at 0 - 10 ℃; for 48h; diastereoselective reaction; Inert atmosphere; Molecular sieve;

DOI:10.1016/j.tet.2016.03.043

Reference yield:

3-ethoxy-2-benzamido-3-oxopropanoic acid (84337-81-5) + 4-nitrobenzaldehdye (555-16-8) → ethyl (2S,3S)-2-benzamido-3-hydroxy-3-(4-nitrophenyl)propanoate + erythro-N-Benzoyl-β-(p-nitro-phenyl)-serinethylester (19185-38-7,19185-39-8,101976-78-7) + ethyl 2-benzamido-3-hydroxy-3-(4-nitrophenyl)propanoate

Guidance literature:

With C₂₉H₂₉N₃O₂S; In tetrahydrofuran; at 20 ℃; for 48h; Overall yield = 41 %; stereoselective reaction; Inert atmosphere;

DOI:10.1055/s-0036-1588141

upstream raw materials:

3-ethoxy-2-benzamido-3-oxopropanoic acid

4-nitrobenzaldehdye

erythro-DL-p-nitrophenylserine ethyl ester hydrochloride

benzoyl chloride

Downstream raw materials:

(1RS,2RS)-2-benzoylamino-1-(4-nitro-phenyl)-propane-1,3-diol

(2RS,3RS)-2-amino-3-benzoyloxy-3-(4-nitro-phenyl)-propionic acid ethyl ester; hydrochloride

5c-(4-nitro-phenyl)-2-phenyl-4,5-dihydro-oxazole-4r-carboxylic acid ethyl ester

(2RS,3SR)-2-benzoylamino-3-chloro-3-(4-nitro-phenyl)-propionic acid ethyl ester