Chloramphenicol dipalmitate

Base Information

• Chemical Name: Chloramphenicol dipalmitate
• CAS No.: 17709-53-4
• Molecular Formula: C₄₃H₇₂Cl₂N₂O₇
• Molecular Weight: 799.96
• UNII: MN3D3TXF2Z
• DSSTox Substance ID: DTXSID401118684
• Nikkaji Number: J2.956.643G
• Mol file: 17709-53-4.mol

Synonyms:Chloramphenicol dipalmitate;MN3D3TXF2Z;Chloramphenicol 1',3'-dipalmitate;17709-53-4;Chloramphenicol palmitate ep impurity B;(1R,2R)-2-((Dichloroacetyl)amino)-1-(4-nitrophenyl)propane-1,3-diyl bishexadecanoate;Hexadecanoic acid, 1,1'-((1R,2R)-2-((2,2-dichloroacetyl)amino)-1-(4-nitrophenyl)-1,3-propanediyl) ester;Hexadecanoic acid, 2-((dichloroacetyl)amino)-1-(4-nitrophenyl)-1,3-propanediyl ester, (R-(R*,R*))-;UNII-MN3D3TXF2Z;DTXSID401118684;1,1'-[(1R,2R)-2-[(2,2-Dichloroacetyl)amino]-1-(4-nitrophenyl)-1,3-propanediyl] dihexadecanoate;PALMITIC ACID, DIESTER WITH 2,2-DICHLORO-N-(.BETA.-HYDROXY-.ALPHA.-(HYDROXYMETHYL)-P-NITROPHENETHYL)ACETAMIDE, (+)-;Palmitic acid, diester with 2,2-dichloro-N-(beta-hydroxy-alpha-(hydroxymethyl)-p-nitrophenethyl)acetamide, (+)-

Chemical Property of Chloramphenicol dipalmitate

Chemical Property:

• XLogP3: 16.7
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 7
• Rotatable Bond Count: 37
• Exact Mass: 798.4716580
• Heavy Atom Count: 54
• Complexity: 957

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CCCCCCCCCCCCCCCC(=O)OCC(C(C1=CC=C(C=C1)[N+](=O)[O-])OC(=O)CCCCCCCCCCCCCCC)NC(=O)C(Cl)Cl
• Isomeric SMILES: CCCCCCCCCCCCCCCC(=O)OC[C@H]([C@@H](C1=CC=C(C=C1)[N+](=O)[O-])OC(=O)CCCCCCCCCCCCCCC)NC(=O)C(Cl)Cl

Technology Process of Chloramphenicol dipalmitate

There total 3 articles about Chloramphenicol dipalmitate 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: 71.0%

chloramphenicol (56-75-7,85666-84-8) + n-hexadecanoyl chloride (112-67-4) → (1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate (17709-53-4)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h; Inert atmosphere;

DOI:10.1016/j.tet.2011.02.070

Reference yield:

vinyl palmitate (693-38-9) + chloramphenicol (56-75-7,85666-84-8) → (1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate (17709-53-4) + chloramphenicol Palmitate (530-43-8) + (1R,2R)-2-[(dichloroacetyl)amino]-3-hydroxy-1-(4-nitrophenyl)propyl hexadecanoate (93464-25-6)

Guidance literature:

With palmitic acid imprinted Thermomyces lanuginosus Lypozyme TL 100L lipase nanogel; In acetone; at 30 ℃; for 48h; Solvent; Green chemistry; Enzymatic reaction;

DOI:10.1039/c3gc40465j

Reference yield:

(1R,2R)-3-(acetyloxy)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)propyl acetate (10318-17-9) → (1R,2R)-2-[(dichloroacetyl)amino]-1-(4-nitrophenyl)-3-(palmitoyloxy)propyl palmitate (17709-53-4)

Guidance literature:

Multi-step reaction with 2 steps

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

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

With dmap; triethylamine; In dichloromethane; acetonitrile;

DOI:10.1016/j.tet.2011.02.070

upstream raw materials:

chloramphenicol

n-hexadecanoyl chloride

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

vinyl palmitate