(1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate

Base Information

• Chemical Name: (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate
• CAS No.: 1304534-10-8
• Molecular Formula: C₁₄H₁₆Cl₂N₂O₆
• Molecular Weight: 379.197
• Mol file: 1304534-10-8.mol

Synonyms:(1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate

Chemical Property of (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate

There total 5 articles about (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate 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: 74.0%

(1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(propanoyloxy)propyl propanoate (1304534-01-7) → (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate (1304534-10-8)

Guidance literature:

With Novozym 435; In acetonitrile; at 20 ℃; for 24h; pH=7; regioselective reaction; aq. phosphate buffer; Enzymatic reaction;

DOI:10.1016/j.tet.2011.02.070

Reference yield: 60.0%

1-propanoyl-3-tert-butyldimethylsilychloramphenicol → (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate (1304534-10-8)

Guidance literature:

With toluene-4-sulfonic acid; In tetrahydrofuran; water; at 20 ℃;

DOI:10.1021/acs.jnatprod.7b00903

Reference yield:

chloramphenicol (56-75-7,85666-84-8) → (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl propionate (1304534-10-8)

Guidance literature:

Multi-step reaction with 2 steps

1: dmap; triethylamine / dichloromethane / 1 h / 20 °C / Inert atmosphere

2: Novozym 435 / acetonitrile / 24 h / 20 °C / pH 7 / aq. phosphate buffer; Enzymatic reaction

With dmap; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2011.02.070

upstream raw materials:

(1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(propanoyloxy)propyl propanoate

chloramphenicol

(1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate

chloramphenicol