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Basic Information
CAS No.: 204255-11-8
Name: Oseltamivir phosphate
Molecular Structure:
Molecular Structure of 204255-11-8 (Oseltamivir phosphate)
Formula: C16H28N2O4.H3PO4
Molecular Weight: 410.404
Synonyms: Oseltamivir Phosphate [USAN];ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxy-cyclohexene-1-carboxylate; phosphoric acid;GS4104;Ro-64-0796;Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate phosphate (1:1);Tamiflu (TN);GS4071;Tamiflu (*Phosphate salt 1:1*);1-Cyclohexene-1-carboxylic acid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)-, phosphate (1:1);Oseltamivir phosphate (JAN/USAN);
Density: 1.08g/cm3
Melting Point: 196-198°C
Boiling Point: 473.3 °C at 760 mmHg
Flash Point: 240 °C
Appearance: white cyrstalline solid
PSA: 178.22000
LogP: 1.44800
Synthetic route
196618-13-0

oseltamivir

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
With phosphoric acid In ethanol at 50℃; for 0.0166667h; Sonication;98%
With phosphoric acid In ethanol at -18.8℃; for 17h;89.9%
With phosphoric acid In ethanol at 50 - 55℃;88.6%

ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With palladium 10% on activated carbon; 2,2'-iminobis[ethanol] In ethanol at 68 - 78℃; for 8h;
Stage #2: With phosphoric acid In ethanol at 45 - 55℃; Reagent/catalyst;
96.31%
With 1,3-dimethylbarbituric acid; phosphoric acid; palladium 10% on activated carbon; triphenylphosphine In ethanol at 55 - 78℃; Temperature; Reagent/catalyst; Large scale;89%
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid In dichloromethane at 35℃; for 7h; Inert atmosphere;
Stage #2: With phosphoric acid In ethanol at 48 - 52℃; for 2h;
85%
204255-06-1

oseltamivir

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Stage #1: oseltamivir With tributylphosphine; triphenylphosphine In ethanol; water at 50℃; for 3h;
Stage #2: With phosphoric acid In ethanol
92%
Stage #1: oseltamivir With Lindlar's catalyst; hydrogen In ethanol at 20℃; under 760.051 Torr; for 16h;
Stage #2: With phosphoric acid In ethanol; ethyl acetate at 50℃; for 0.5h;
91%
91%
86119-84-8, 7664-38-2

phosphoric acid

196618-13-0

oseltamivir

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
In ethanol; water at 50 - 55℃; for 1.5 - 2h;88%
367252-68-4

(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
With phosphoric acid In ethanol at 78℃; for 12h; Inert atmosphere;83%
With phosphoric acid In ethanol at 0 - 78℃; for 15h; Inert atmosphere;83%
With phosphoric acid In ethanol at 50℃; for 6h;81%

(3R,4R,5S)-4-acetamido-5-allyloxycarbonylamino-1-ethoxycarbonyl-3-(3-pentyloxy)cyclohex-1-ene

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Stage #1: (3S,4S,5S)-4-acetamido-5-allyloxycarbonylamino-1-ethoxycarbonyl-3-(3-pentyloxy)cyclohex-2-ene With 1,3-dimethylbarbituric acid; 5%-palladium/activated carbon; triphenylphosphine In ethanol at 80℃; for 1h;
Stage #2: With phosphoric acid In ethanol at 50℃;
76%
891831-22-4

tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate

64-17-5

ethanol

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Stage #1: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate; ethanol With hydrogenchloride at 60℃; for 4h;
Stage #2: With phosphoric acid at 4 - 50℃;
50%
Stage #1: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate; ethanol With hydrogenchloride
Stage #2: With sodium hydroxide
Stage #3: With phosphoric acid

(2-oxo-2,3,3aβ,4α,5,7aβ-hexahydro-benzoxazol-4-yl)-carbamic acid tert-butyl ester

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1.1: LiOH
1.2: NEt3
2.1: isobutyric anhydride; DMSO
3.1: Ni(cod)2; 1,5-cyclooctadiene
3.2: NBS; NEt3
4.1: LiAl(Ot-Bu)3H
5.1: DEAD; PPh3
5.2: 56 percent / BF3*OEt2
6.1: HCl
6.2: aq. NaOH
6.3: H3PO4
View Scheme
930275-48-2

(1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1.1: Ni(cod)2; 1,5-cyclooctadiene
1.2: NBS; NEt3
2.1: LiAl(Ot-Bu)3H
3.1: DEAD; PPh3
3.2: 56 percent / BF3*OEt2
4.1: HCl
4.2: aq. NaOH
4.3: H3PO4
View Scheme

(6-acetylamino-5-hydroxy-cyclohex-3-enyl)-carbamic acid tert-butyl ester

204255-11-8

oseltamivir phosphate

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1.1: isobutyric anhydride; DMSO
2.1: Ni(cod)2; 1,5-cyclooctadiene
2.2: NBS; NEt3
3.1: LiAl(Ot-Bu)3H
4.1: DEAD; PPh3
4.2: 56 percent / BF3*OEt2
5.1: HCl
5.2: aq. NaOH
5.3: H3PO4
View Scheme
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196618-13-0
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History

In Japan, Oseltamivir(204255-11-8) is marketed by Chugai Pharmaceutical Co., which is more than 50% owned by Roche

Consensus Reports

Oseltamivir(204255-11-8) acts as a transition-state analogue inhibitor of influenza neuraminidase, preventing progeny virions from detaching from infected cells.

Specification

The Oseltamivir phosphate, with its CAS registry number 204255-11-8, has the IUPAC name of ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate; phosphoric acid. For being a kind of white cyrstalline solid, it is usually applied as an antiviral drug, with its product categories including API; Intermediates & Fine Chemicals; Pharmaceuticals; Ring Systems; Oseltamivir; Influenza Viruses.

The characteristics of this chemical are as below: (1)ACD/LogP: 1.50; (2)# of Rule of 5 Violations: 0; (3)ACD/LogD (pH 5.5): -1.02; (4)ACD/LogD (pH 7.4): 0.69; (5)ACD/BCF (pH 5.5): 1; (6)ACD/BCF (pH 7.4): 1.25; (7)ACD/KOC (pH 5.5): 1; (8)ACD/KOC (pH 7.4): 24.06; (9)#H bond acceptors: 6; (10)#H bond donors: 3; (11)#Freely Rotating Bonds: 9; (12)Polar Surface Area: 59.08; (13)Flash Point: 240 °C; (14)Enthalpy of Vaporization: 73.64 kJ/mol; (15)Boiling Point: 473.3 °C at 760 mmHg; (16)Vapour Pressure: 3.98E-09 mmHg at 25°C; (17)Exact Mass: 410.181802; (18)MonoIsotopic Mass: 410.181802; (19)Topological Polar Surface Area: 168; (20)Heavy Atom Count: 27; (21)Complexity: 468.

What's more, the following datas could be converted into the molecular structure:
(1)Canonical SMILES: CCC(CC)OC1C=C(CC(C1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
(2)Isomeric SMILES: CCC(CC)O[C@@H]1C=C(C[C@@H]([C@H]1NC(=O)C)N)C(=O)OCC.OP(=O)(O)O
(3)InChI: InChI=1S/C16H28N2O4.H3O4P/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19;1-5(2,3)4/h9,12-15H,5-8,17H2,1-4H3,(H,18,19);(H3,1,2,3,4)/t13-,14+,15+;/m0./s1
(4)InChIKey: PGZUMBJQJWIWGJ-ONAKXNSWSA-N