rac-Febrifugine Dihydrochloride

Base Information

• Chemical Name: rac-Febrifugine Dihydrochloride
• CAS No.: 32434-42-7
• Molecular Formula: C₁₆H₁₉N₃O₃*2ClH
• Molecular Weight: 374.267
• Mol file: 32434-42-7.mol

Synonyms:

Chemical Property of rac-Febrifugine Dihydrochloride

Chemical Property:

• Melting Point: 220-222 °C (decomp)
• Storage Temp.: ?20°C
• Solubility.: H2O: soluble15mg/mL, clear

Purity/Quality:

98%,99%, ^*data from raw suppliers

Febrifugine dihydrochloride ≥95% (HPLC) ^*data from reagent suppliers

Safty Information:

• Hazard Codes: Xn
• Statements: 22

MSDS Files:

Useful:

• Uses: rac-Febrifugine dihydrochloride is the salt of Febrifugine, a bioactive constituent of a Chinese medicinal herb that is characterized by its therapeutic activity regarding malaria, cancer, fibrosis and inflammatory diseases.

Technology Process of rac-Febrifugine Dihydrochloride

There total 7 articles about rac-Febrifugine Dihydrochloride 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: 76.0%

(+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate (1185729-94-5) → febrifugine dihydrochloride (27257-66-5,32434-42-7)

Guidance literature:

With hydrogenchloride; palladium on carbon; hydrogen; In methanol; water; for 2h; under 760.051 Torr;

DOI:10.1039/b901670h

Reference yield:

(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester (1203455-37-1) → febrifugine dihydrochloride (27257-66-5,32434-42-7)

Guidance literature:

With hydrogenchloride; water;

DOI:10.1016/j.tetlet.2020.152151

Reference yield:

C16H23N3O4S → febrifugine dihydrochloride (27257-66-5,32434-42-7)

Guidance literature:

Multi-step reaction with 6 steps

1.1: triphenylphosphine / tetrahydrofuran / 1 h

1.2: 0.25 h

1.3: 10 h / 50 - 55 °C

2.1: triethylamine / dichloromethane / 0 °C

3.1: palladium dichloride; oxygen; copper(l) chloride / N,N-dimethyl-formamide; water

4.1: trimethylsilyl trifluoromethanesulfonate; N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C / Inert atmosphere

4.2: 1.5 h / 0 - 20 °C / Inert atmosphere

5.1: potassium carbonate / N,N-dimethyl-formamide / 16 h / 20 °C

6.1: hydrogenchloride; water

With hydrogenchloride; trimethylsilyl trifluoromethanesulfonate; water; oxygen; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; copper(l) chloride; palladium dichloride; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; 1.1: |Staudinger Azide Reduction / 1.2: |Staudinger Azide Reduction / 1.3: |Staudinger Azide Reduction;

DOI:10.1016/j.tetlet.2020.152151

upstream raw materials:

(+)-(2S,3R)-benzyl 3-hydroxy-2-(2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl)piperidine-1-carboxylate

(2S,3R)-3-benzyloxy-2-(2-oxopropyl)piperidine-1-carboxylic acid benzyl ester

(2S,3R)-3-benzyloxy-2-[2-oxo-3-(4-oxoquinazolin-3(4H)-yl)propyl]piperidine-1-carboxylic acid benzyl ester

Refernces

• 1、 Wijdeven, Marloes A.,Van Den Berg, Rutger J. F.,Wijtmans, Roel,Botman, Peter N. M.,Blaauw, Richard H.,Schoemaker, Hans E.,Van Delft, Floris L.,Rutjes, Floris P. J. T.. "Complementary chemoenzymatic routes to both enantiomers of febrifugine". experimental part. p. 2976 - 2980. Retrieved 2011/02/26.