OseltaMivir IMpurity A

Base Information

• Chemical Name: OseltaMivir IMpurity A
• CAS No.: 1364932-19-3
• Molecular Formula: C₁₄H₂₄N₂O₄
• Molecular Weight: 284.356
• Mol file: 1364932-19-3.mol

Synonyms:

Chemical Property of OseltaMivir IMpurity A

Chemical Property:

• Boiling Point: 508.7±50.0 °C(Predicted)
• PKA: 3.51±0.60(Predicted)
• Density: 1.15±0.1 g/cm3(Predicted)

Purity/Quality:

NLT 98% ^*data from raw suppliers

Oseltamivir impurity A European Pharmacopoeia (EP) Reference Standard ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: Desethyl Oseitamivir is an impurity of the antiviral drug oseltamivir.

Technology Process of OseltaMivir IMpurity A

There total 8 articles about OseltaMivir IMpurity A 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: 80.0%

(3R,4R,5S)-5-(acetylamino)-4-[(tert-butoxycarbonyl)amino]-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid → (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid (1364932-19-3,1391047-93-0)

Guidance literature:

With isopropyl alcohol hydrogen chloride; In dichloromethane; at 0 - 30 ℃; for 5h;

DOI:10.14233/ajchem.2018.21376

Reference yield:

oseltamivir (196618-13-0) → oseltamivir acid (187227-45-8) + (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid (1364932-19-3,1391047-93-0) + ethyl-(3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

Guidance literature:

In water; at 70 ℃; pH=2 - 8; Kinetics; Product distribution;

DOI:10.1023/A:1011964529805

Reference yield:

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester (204254-96-6,1217834-81-5,1266663-89-1,2413185-89-2) → (3R,4R,5S)-5-(acetylamino)-4-amino-3-(pentan-3-yloxy) cyclohex-1-ene-1-carboxylic acid (1364932-19-3,1391047-93-0)

Guidance literature:

Multi-step reaction with 8 steps

1: ammonium chloride; sodium azide / methanol; water / 65 - 70 °C

2: triphenylphosphine / acetonitrile / 3.25 h / 20 - 80 °C

3: ammonium chloride; sodium azide / N,N-dimethyl-formamide / 16 h / 65 - 70 °C

4: triethylamine / dichloromethane / 16 h / 0 - 20 °C

5: triphenylphosphine / tetrahydrofuran / 16 h / 25 - 30 °C

6: potassium carbonate / tetrahydrofuran / 4 h / 20 °C

7: lithium hydroxide monohydrate / water; tetrahydrofuran / 7 h / 20 °C

8: isopropyl alcohol hydrogen chloride / dichloromethane / 5 h / 0 - 30 °C

With sodium azide; isopropyl alcohol hydrogen chloride; lithium hydroxide monohydrate; potassium carbonate; ammonium chloride; triethylamine; triphenylphosphine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide; acetonitrile;

DOI:10.14233/ajchem.2018.21376

upstream raw materials:

oseltamivir

(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

ethyl-(3R,4S,5R)-5-azido-4-hydroxy-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

ethyl-(1R,5R,6R)-5-(pentan-3-yloxy)-7-azabicyclo[4.1.0]hept-3-ene-3-carboxylate