Ethylhydrocupreine

Base Information

• Chemical Name: Ethylhydrocupreine
• CAS No.: 522-60-1
• Molecular Formula: C21H28 N2 O2
• Molecular Weight: 340.466
• Hs Code.: 2933990090
• European Community (EC) Number: 208-333-5
• UNII: 4W030VS2OG
• DSSTox Substance ID: DTXSID50893924
• Wikipedia: Optochin
• ChEMBL ID: CHEMBL548228
• Mol file: 522-60-1.mol

Synonyms:ethylhydrocupreine;ethylhydrocupreine monohydrochloride;Numoquin;Optochin;Optochine;Optoquine

Chemical Property of Ethylhydrocupreine

Chemical Property:

• Vapor Pressure: 3.59E-11mmHg at 25°C
• Melting Point: 123-128° when solvent-free
• Refractive Index: 1.6180 (estimate)
• Boiling Point: 508.7°Cat760mmHg
• Flash Point: 261.5°C
• PSA: 45.59000
• Density: 1.18g/cm³
• LogP: 3.72520
• Storage Temp.: 2-8°C
• XLogP3: 3.5
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 5
• Exact Mass: 340.215078140
• Heavy Atom Count: 25
• Complexity: 446

Purity/Quality:

99%, ^*data from raw suppliers

Ethylhydrocupreine ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xn
• Hazard Codes: Xn
• Statements: 22

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: CCC1CN2CCC1CC2C(C3=C4C=C(C=CC4=NC=C3)OCC)O
• Isomeric SMILES: CC[C@H]1CN2CC[C@H]1C[C@H]2[C@@H](C3=C4C=C(C=CC4=NC=C3)OCC)O
• Uses: Ethylhydrocupreine is an antibiotic tested against isolates of Streptococcus mitis resulting in an 100% resistance. Also, ethylhydrocupreine susceptibility test is a key method for differentiating Streptococcus pneumoniae from other α-hemolytic streptococci.

Technology Process of Ethylhydrocupreine

There total 8 articles about Ethylhydrocupreine 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: 63.0%

ethyl bromide (74-96-4) + (8α,9R)-10,11-dihydro-cinchonan-6',9-diol (5962-19-6) → (R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline (522-60-1)

Guidance literature:

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol; With caesium carbonate; In N,N-dimethyl-formamide; for 0.166667h;

ethyl bromide; In N,N-dimethyl-formamide; for 3h;

DOI:10.1021/acs.jmedchem.8b01353

Reference yield:

→ (R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline (522-60-1)

Guidance literature:

With sulphurous acid; at 80 ℃; im Autoklaven;

Reference yield:

Quinine (130-95-0) → (R)-4-((1S,2S,4S,5R)-5-ethyl-1-azabicyclo[2.2.2]octan-2-yl)hydroxymethyl-6-ethoxyquinoline (522-60-1)

Guidance literature:

Multi-step reaction with 3 steps

1.1: palladium on carbon; hydrogen / 72 h

2.1: sodium hydride; ethanethiol / mineral oil; N,N-dimethyl-formamide / 13 h / 100 °C

3.1: caesium carbonate / N,N-dimethyl-formamide / 0.17 h

3.2: 3 h

With palladium on carbon; hydrogen; sodium hydride; caesium carbonate; ethanethiol; In N,N-dimethyl-formamide; mineral oil;

DOI:10.1021/acs.jmedchem.8b01353

upstream raw materials:

diethyl sulfate

4-((S)-((1S,2R,4S,5R)-5-ethylquinuclidin-2-yl)(hydroxy)methyl)quinolin-6-ol

(8α,9R)-10,11-dihydro-cinchonan-6',9-diol

chloroethane

Downstream raw materials:

6-ethoxy-quinoline-4-carboxylic acid

Refernces