L-erythro-Chloramphenicol

Base Information

• Chemical Name: L-erythro-Chloramphenicol
• CAS No.: 7384-89-6
• Molecular Formula: C11H12 Cl2 N2 O5
• Molecular Weight: 323.133
• Hs Code.: 2924299090
• NSC Number: 756677
• DSSTox Substance ID: DTXSID80224388
• Wikidata: Q27188691
• Mol file: 7384-89-6.mol

Synonyms:L-erythro-Chloramphenicol;7384-89-6;L(+)-erythro-Chloramphenicol;2,2-dichloro-N-[(1R,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl]acetamide;Acetamide, 2,2-dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)-, (R-(R*,S*))-;(R-(R*,S*))-2,2-Dichloro-N-(2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl)acetamide;2,2-dichloro-N-((1R,2S)-1,3-dihydroxy-1-(4-nitrophenyl)propan-2-yl)acetamide;C11-H12-Cl2-N2-O5;Acetamide, 2,2-dichloro-N-[2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]-, [R-(R*,S*)]-;Spectrum_001311;Spectrum2_000884;Spectrum3_000338;Spectrum4_000275;Spectrum5_001334;BSPBio_001975;KBioGR_000770;KBioSS_001791;SPECTRUM1500174;SPBio_000668;KBio2_001791;KBio2_004359;KBio2_006927;KBio3_001195;DTXSID80224388;CHEBI:109546;HMS1920M19;HMS2091C08;Pharmakon1600-01500174;Acetamide, 2,2-dichloro-N-[.beta.-hydroxy-.alpha.-(hydroxymethyl)-p-nitrophenethyl]-, L-erythro-()-;CCG-39895;NSC756677;AKOS015960195;AKOS040746069;NSC-756677;NCGC00178884-01;NCGC00178884-02;AC-10036;SBI-0051289.P003;AB00051919_02;SR-05000001585;SR-05000001585-1;BRD-K22969690-001-02-6;BRD-K22969690-001-03-4;Q27188691;2,2-dichloro-N-[(1S,2R)-2-hydroxy-1-(hydroxymethyl)-2-(4-nitrophenyl)ethyl]acetamide

Chemical Property of L-erythro-Chloramphenicol

Chemical Property:

• Melting Point: 176 °C
• Boiling Point: 644.9±55.0 °C(Predicted)
• PKA: 11.03±0.46(Predicted)
• PSA: 115.38000
• Density: 1.547±0.06 g/cm3(Predicted)
• LogP: 1.82310
• Storage Temp.: -20°C Freezer
• Solubility.: DMSO (Slightly), Ethanol (Slightly), Methanol (Slightly)
• XLogP3: 1.1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 5
• Exact Mass: 322.0123269
• Heavy Atom Count: 20
• Complexity: 342

Purity/Quality:

L-erythro-Chloramphenicol ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: C1=CC(=CC=C1C(C(CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Isomeric SMILES: C1=CC(=CC=C1[C@H]([C@H](CO)NC(=O)C(Cl)Cl)O)[N+](=O)[O-]
• Uses: L-erythro-Chloramphenicol functions as a potent inhibitor of electron transport in the mitochondria in biological studies. The L-isomer can be identified from the other CAP-isomers through reversed phase and chiral liquid chromatography in combination with tandem mass spectrometric detection.

Technology Process of L-erythro-Chloramphenicol

There total 72 articles about L-erythro-Chloramphenicol 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: 79.0%

(2RS,3SR)-2-(2,2-dichloro-acetylamino)-3-hydroxy-3-(4-nitro-phenyl)-propionic acid ethyl ester (100381-03-1) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With sodium tetrahydroborate; In methanol; at 0 ℃; for 0.5h;

DOI:10.1021/ol901784m

Reference yield:

chloramphenicol (26367-75-9) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

With aluminum isopropoxide; isopropyl alcohol;

DOI:10.1021/ja01145a523

Reference yield:

(+/-)-threo-2-amino-1-phenyl-1,3-propanediol (3306-06-7,5285-86-9,28143-91-1,36391-67-0,36391-68-1,46032-98-8,55057-81-3,105452-39-9,119364-52-2) → chlorampenicol (56-75-7,134-90-7,579-51-1,2787-09-9,3419-87-2,7384-89-6,7387-98-6,50762-99-7,126787-77-7,140694-65-1,85666-84-8)

Guidance literature:

Multi-step reaction with 5 steps

2: pyridine

3: amidosulfuric acid; nitric acid

4: aqueous hydrochloric acid

With pyridine; hydrogenchloride; aminosulfonic acid; nitric acid;

DOI:10.1021/ja01175a066

upstream raw materials:

dichloroacetic acid methyl ester

(1R,2S)-(+)-2-amino-1-(4-nitrophenyl)-1,3-propanediol

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

(1R,2S)-2-benzoylamino-3-benzoyloxy-1-(4-nitro-phenyl)-propan-1-ol

Downstream raw materials:

chloramphenicol

L-threo-chloramphenicol

dichloroacetic acid-[4t-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide]

dichloroacetic acid-[4c-(4-nitro-phenyl)-2ξ-oxo-2λ⁴-[1,3,2]dioxathian-5r-ylamide]

Refernces

• 1、 Singjunla, Yuttapong,Baudoux, Jeroime,Rouden, Jacques. "Direct synthesis of β-hydroxy-α-amino acids via diastereoselective decarboxylative aldol reaction". . p. 5770 - 5773. Retrieved 2013/12/04.
• 2、 Hazra, Braja G.,Pore, Vandana S.,Maybhate, Shailaja P.. "Synthesis of chloramphenicol via a new intermediate 4-para-nitrophenyl- 5-formamido-1,3-dioxane". . p. 1857 - 1864. Retrieved 2007/10/03.