(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate

Base Information

• Chemical Name: (R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate
• CAS No.: 681490-95-9
• Molecular Formula: C₁₄H₁₃ClN₄O₇
• Molecular Weight: 384.733
• DSSTox Substance ID: DTXSID001123176
• Mol file: 681490-95-9.mol

Synonyms:681490-95-9;(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate;[(2R)-3-(2-chloro-4-nitroimidazol-1-yl)-2-hydroxy-2-methylpropyl] 4-nitrobenzoate;SCHEMBL19542442;DTXSID001123176

Chemical Property of (R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate

Chemical Property:

• Melting Point: 122-123 °C(Solv: ethyl acetate (141-78-6); isopropyl ether (108-20-3))
• Boiling Point: 638.9±65.0 °C(Predicted)
• Density: 1.58±0.1 g/cm3(Predicted)
• XLogP3: 2
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 6
• Exact Mass: 384.0472765
• Heavy Atom Count: 26
• Complexity: 546

Purity/Quality:

95%-98% ^*data from raw suppliers

(R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl4-Nitrobenzoate ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Canonical SMILES: CC(CN1C=C(N=C1Cl)[N+](=O)[O-])(COC(=O)C2=CC=C(C=C2)[N+](=O)[O-])O
• Isomeric SMILES: C[C@@](CN1C=C(N=C1Cl)[N+](=O)[O-])(COC(=O)C2=CC=C(C=C2)[N+](=O)[O-])O
• Uses: (R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate is an intermediate in the synthesis of Delamanid (D230660), a novel anti-tuberculosis medication that inhibits mycolic acid synthesis and shows potent in-vitro and in-vivo activity against drug-resistant strains of Mycobacterium tuberculosis.

Technology Process of (R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate

There total 2 articles about (R)-3-(2-Chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropyl 4-Nitrobenzoate 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: 87.0%

2-chloro-4-nitro-1H-imidazole (57531-37-0) + (2R)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane (106268-96-6) → (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole (681490-95-9)

Guidance literature:

With triethylamine; In ethyl acetate; at 60 - 65 ℃; for 6h;

DOI:10.1021/jm060957y

Reference yield:

(R)-glycidyl 4-nitrobenzoate (106268-95-5) + 2-chloro-4-nitro-1H-imidazole (57531-37-0) → (R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole (681490-95-9)

Guidance literature:

With triethylamine; In ethyl acetate; at 60 - 65 ℃; for 6h;

Reference yield:

(R)-2-chloro-1-[2-hydroxy-2-methyl-3-(4-nitrobenzoyloxy)]-propyl-4-nitroimidazole (681490-95-9) → 2-(4-chloro-phenoxymethyl)-2-methyl-6-nitro-2,3-dihydro-imidazo[2,1-b]oxazole

Guidance literature:

Multi-step reaction with 4 steps

1: 97 percent / K₂CO₃ / methanol / 2 h / 20 °C

2: pyridine / 2.5 h / 15 °C

3: 6.93 g / DBU / ethyl acetate / 2 h / 20 °C

4: NaH / dimethylformamide / 2 h / 50 °C

With pyridine; sodium hydride; potassium carbonate; 1,8-diazabicyclo[5.4.0]undec-7-ene; In methanol; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1021/jm060957y

upstream raw materials:

2-chloro-4-nitro-1H-imidazole

(2R)-methyl-3-[4-nitrobenzoyl(oxy)]-1,2-epoxy-propane

(R)-glycidyl 4-nitrobenzoate

Downstream raw materials:

(R)-2-chloro-1-(2,3-dihydroxy-2-methyl)-propyl-4-nitroimidazole

2-chloro-1-{[(2R)-2-methyloxiran-2-yl]methyl}-4-nitro-1H-imidazole

(R)-3-(2-chloro-4-nitro-1H-imidazol-1-yl)-2-hydroxy-2-methylpropylmethanesulfonate

2-methyl-6-nitro-2-(4-thiomorpholin-4-yl-phenoxymethyl)-2,3-dihydro-imidazo[2,1-b]oxazole

Refernces

• 1、 Munagala, Gurunadham,Yempalla, Kushalava Reddy,Singh, Samsher,Sharma, Sumit,Kalia, Nitin Pal,Rajput, Vikrant Singh,Kumar, Sunil,Sawant, Sanghapal D.,Khan, Inshad Ali,Vishwakarma, Ram A.,Singh, Parvinder Pal. "Synthesis of new generation triazolyl- and isoxazolyl-containing 6-nitro-2,3-dihydroimidazooxazoles as anti-TB agents: In vitro, structure-activity relationship, pharmacokinetics and in vivo evaluation". supporting information. p. 3610 - 3624. Retrieved 2015/03/30.
• 2、 Sasaki, Hirofumi,Haraguchi, Yoshikazu,Itotani, Motohiro,Kuroda, Hideaki,Hashizume, Hiroyuki,Tomishige, Tatsuo,Kawasaki, Masanori,Matsumoto, Makoto,Komatsu, Makoto,Tsubouchi, Hidetsugu. "Synthesis and antituberculosis activity of a novel series of optically active 6-nitro-2,3-dihydroimidazo[2,1-b]oxazoles". . p. 7854 - 7860. Retrieved 2007/10/03.