Oseltamivir acid

Base Information

• Chemical Name: Oseltamivir acid
• CAS No.: 187227-45-8
• Molecular Formula: C₁₄H₂₄N₂O₄
• Molecular Weight: 284.356
• Hs Code.: 9999999999
• UNII: K6106LV5Q8
• DSSTox Substance ID: DTXSID50171996
• Nikkaji Number: J820.936G
• Wikidata: Q27140336
• RXCUI: 1546279
• Metabolomics Workbench ID: 66274
• ChEMBL ID: CHEMBL674
• Mol file: 187227-45-8.mol

Synonyms:Oseltamivir acid;187227-45-8;Oseltamivir carboxylate;GS 4071;GS4071;Ro 64-0802;Oseltamivir free acid;GS-4071;Ro-64-0802;Oseltamivir-carboxylate;Oseltamivir acid, (-)-;CHEMBL674;UNII-K6106LV5Q8;CHEBI:73139;K6106LV5Q8;(3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylic acid;(3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid;1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, (3R,4R,5S)-;RO-640802;204255-09-4 (HCl);(3r,4r,5s)-4-(Acetylamino)-5-Amino-3-(Pentan-3-Yloxy)cyclohex-1-Ene-1-Carboxylic Acid;(3R,4R,5S)-5-amino-4-acetamido-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid;G39;Oseltamivir Carboxylic Acid;Oseltamiviracid;Oseltamivir (acid);2,4-diamino triazine;Oseltamivir EP Impurity C;D06IDO;D0YY3N;SCHEMBL182903;BDBM4994;DTXSID50171996;AKOS027325283;CS-0553;CS-O-10285;DB02600;HY-13318;C90284;EN300-150145;A907638;OSELTAMIVIR PHOSPHATE IMPURITY C [EP IMPURITY];Q27140336;OSELTAMIVIR PHOSPHATE IMPURITY, OSELTAMIVIR ACID- [USP IMPURITY];(3R,4R,5S)-4-(Acetylamino)-5-amino-3-(1-ethylpropoxy)-1-cyclohexence-1-carboxylic Acid;(3R,4R,5S)-4-Acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohex-ene-1-carboxylic acid;(3R,4R,5S)-4-ACETAMIDO-5-AMINO-3-(1-ETHYLPROPOXY)CYCLOHEX-1-ENE-1-CARBOXYLIC ACID;(3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)cyclohexene-1-carboxylic acid;(3r,4r,5s)-4-acetylamino-5-amino-3(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid;(3r,4r,5s)-4-acetylamino-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid;1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, (3R-(3alpha,4beta,5alpha))-

Chemical Property of Oseltamivir acid

Chemical Property:

• Vapor Pressure: 1E-11mmHg at 25°C
• Melting Point: 183-185°C
• Boiling Point: 508.7°Cat760mmHg
• PKA: 4.13±0.60(Predicted)
• Flash Point: 261.5°C
• PSA: 101.65000
• Density: 1.15g/cm³
• LogP: 1.89810
• Storage Temp.: -20?C Freezer, Under Inert Atmosphere
• Solubility.: ≥14.2 mg/mL in DMSO; ≥46.1 mg/mL in H2O with gentle warming; ≥97 mg/mL in EtOH with gentle warming
• XLogP3: -1.9
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 6
• Exact Mass: 284.17360725
• Heavy Atom Count: 20
• Complexity: 391

Purity/Quality:

99% ^*data from raw suppliers

OseltamivirAcid ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)O
• Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)O
• Description: Oseltamivir (GS-4104) is an antiviral prodrug targeted against the influenza viruses. Oseltamivir acid is the active metabolite of oseltamivir. It acts as an inhibitor of influenza neuraminidases A and B (IC50 = 0.1 to 4.9 nM for both enzymes), in this way preventing virus budding and release.
• Uses: Oseltamivir Acid is a metabolite of Oseltamivir (O701000). Oseltamivir Acid (Oseltamivir EP Impurity C) is a metabolite of Oseltamivir (O701000). It is a COVID19-related research product.

Technology Process of Oseltamivir acid

There total 37 articles about Oseltamivir acid 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: 99.0%

oseltamivir (196618-13-0) → oseltamivir acid (187227-45-8)

Guidance literature:

With sodium hydroxide; In ethanol; at 90 ℃; for 2h;

DOI:10.1016/j.bmcl.2008.01.037

Reference yield: 75.0%

methyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (208720-71-2) → oseltamivir acid (187227-45-8)

Guidance literature:

With potassium hydroxide; In tetrahydrofuran; at 20 ℃; for 0.666667h; pH=5.5 - 6;

Reference yield: 42.0%

ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate (1402431-91-7) → (3R,4R,5R)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid (187227-45-8)

Guidance literature:

With sodium hydroxide; In tetrahydrofuran; water; at 0 - 20 ℃; for 3h;

DOI:10.1039/c6ob02673g

upstream raw materials:

methyl (3R,4R,5S)-4-acetamido-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

oseltamivir

2-pentanol

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

Downstream raw materials:

(3R,4R,5S)-4-acetamido-5-[(tert-butoxycarbonyl)-amino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid

(3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid trifluoroacetate

Refernces

• 1、 Neri-Bazán, Rocío M.,García-Machorro, Jazmín,Méndez-Luna, David,Tolentino-López, Luis E.,Martínez-Ramos, Federico,Padilla-Martínez, Itzia I.,Aguilar-Faisal, Leopoldo,Soriano-Ursúa, Marvin A.,Trujillo-Ferrara, José G.,Fragoso-Vázquez, M. Jonathan,Barrón, Blanca L.,Correa-Basurto, José. "Design, in silico studies, synthesis and in?vitro evaluation of oseltamivir derivatives as inhibitors of neuraminidase from influenza A virus H1N1". . p. 154 - 167. Retrieved 2017.
• 2、 Omar, Mahmoud A.,Derayea, Sayed M.,Mostafa, Islam M.. "Development and validation of a stability-indicating spectrofluorimetric method for the determination of H1N1 antiviral drug (oseltamivir phosphate) in human plasma through the Hantzsch reaction". . p. 27735 - 27742. Retrieved 2015.