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| CAS No.: | 204255-11-8 |
|---|---|
| Name: | Oseltamivir phosphate |
| Molecular Structure: | |
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| 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 |
oseltamivir
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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% |
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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% |
oseltamivir
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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% |
| Conditions | Yield |
|---|---|
| In ethanol; water at 50 - 55℃; for 1.5 - 2h; | 88% |
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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% |
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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% |
tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate
ethanol
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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 |
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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 |
(1S,2R)-2-(acetylamino)-1-(tert-butoxycarbonylamino)-4-cyclohexen-3-one
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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 |
oseltamivir phosphate
| Conditions | Yield |
|---|---|
| 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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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
