Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-

Base Information

• Chemical Name: Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-
• CAS No.: 59005-99-1
• Molecular Formula: C₁₅H₁₈Cl₂N₂O₆
• Molecular Weight: 393.224
• ChEMBL ID: CHEMBL4171557
• DSSTox Substance ID: DTXSID101118073
• Mol file: 59005-99-1.mol

Synonyms:SCHEMBL3417156;CHEMBL4171557;DTXSID101118073;59005-99-1;Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-

Chemical Property of Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-

Chemical Property:

• XLogP3: 2.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 9
• Exact Mass: 392.0541917
• Heavy Atom Count: 25
• Complexity: 463

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

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

Technology Process of Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]-

There total 4 articles about Butanoic acid, 2-[(dichloroacetyl)amino]-3-hydroxy-3-(4-nitrophenyl)propyl ester, [R-(R*,R*)]- 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: 85.0%

chloramphenicol (56-75-7,85666-84-8) + butyryl chloride (141-75-3) → 1,3-dibutanoylchloramphenicol + threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-butanoate (59005-99-1)

Guidance literature:

With pyridine; dmap; In dichloromethane; for 0.0833333h;

DOI:10.1021/acs.jnatprod.7b00903

Reference yield:

vinyl n-butyrate (123-20-6,24991-31-9) + chloramphenicol (56-75-7,85666-84-8) → threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-butanoate (59005-99-1)

Guidance literature:

With lipase cloned from Bacillus amyloliquefaciens; In ethanol; at 50 ℃; for 4h; regioselective reaction; Inert atmosphere; Enzymatic reaction;

DOI:10.3390/molecules22091523

Reference yield:

butanoic acid methyl ester (623-42-7) + chloramphenicol (56-75-7,85666-84-8) → threo-(1R,2R)-1-(4-nitrophenyl)-2-(dichloroacetamido)-1,3-propanediol 3-butanoate (59005-99-1)

Guidance literature:

at 45 ℃; for 7h; lipase, molecular sieve;

DOI:10.1021/jo00295a025

upstream raw materials:

butanoic acid methyl ester

chloramphenicol

2,2,2-trifluoroethylbutyrate

vinyl n-butyrate