Oseltamivir supplier | CasNO.196618-13-0

Name
Oseltamivir
EINECS 1308068-626-2
CAS No. 196618-13-0
Article Data66
CAS DataBase
Density 1.08 g/cm³
Solubility Soluble
Melting Point 107-108 °C
Formula C₁₆H₂₈N₂O₄
Boiling Point 473.3 °C at 760 mmHg
Molecular Weight 312.409
Flash Point 240 °C
Transport Information
Appearance
Safety
Risk Codes
Molecular Structure
Hazard Symbols
Synonyms 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, [3R-(3a,4b,5a)]-;GOP-A-Flu;GS 4104;Tamiflu-Free;Tamvir;
PSA 90.65000
LogP 2.37660

Synthetic route

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

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With 1,3-dimethylbarbituric acid; tetrakis(triphenylphosphine) palladium(0) In tetrahydrofuran at 50℃; for 2.21667h;	88.7%
Stage #1: ethyl (3R,4R,5S)-4-N-acetylamino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate With 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine In ethanol at 35℃; for 2h; Inert atmosphere; Stage #2: With phosphoric acid In acetone for 2h;	83.69%
With tetrakis(triphenylphosphine) palladium(0); 1,3-dimethylbarbituric acid

: 367252-68-4
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 20℃; for 4h; Inert atmosphere;	92%
Stage #1: (3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate With hydrogenchloride; water In ethanol at 50℃; for 1h; Stage #2: With sodium hydrogencarbonate In water	90%
With hydrogenchloride In tetrahydrofuran; ethyl acetate for 0.05h;	13.8 mg

: 312904-18-0
ethyl (3R,4R,5S)-4-N-acetylamino-5-N-allylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With ethanolamine; palladium 10% on activated carbon In ethanol at 20℃; for 3h; Heating / reflux;	70%
With palladium on activated charcoal; ethanolamine In ethanol for 3h; Heating;
With ethanolamine; palladium on activated charcoal In ethanol for 3h; Heating;

: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 23 - 70℃; for 2h; Inert atmosphere; Stage #2: With ammonia In ethanol at 0℃; for 0.166667h; Stage #3: With potassium carbonate In ethanol at 23℃; for 6h;	85%
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h; Inert atmosphere; Stage #2: With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere; Stage #3: With potassium carbonate In ethanol at 23℃; for 9h; Inert atmosphere;	81%
Stage #1: (1S,2R,3S,4R,5S)-4-acetylamino-3-(1-ethylpropoxy)-5-nitro-2-p-tolylsulfanylcyclohexanecarboxylic acid ethyl ester With chloro-trimethyl-silane; zinc In ethanol at 70℃; for 2h; Stage #2: With ammonia; potassium carbonate In ethanol at 20℃; for 6h;	80%

: 1041262-68-3
(3R,4R,5S)-4-acetamido-5-(1,3-dioxoisoindol-2-yl)-3-(pentyl-3-yloxy)cyclohexyl-ethyl-1-ene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With hydrazine In ethanol at 68℃; for 10h;	100%
With hydrazine In ethanol at 68℃; for 10h; Inert atmosphere;	100%
With hydrazine In ethanol at 68℃; for 11h; Schlenk technique; Inert atmosphere;	86%

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

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With pyrrolidine; tetrakis(triphenylphosphine) palladium(0) In ethanol for 0.5h;	95.1%
With 1,3-dimethylbarbituric acid; triphenylphosphine; palladium on activated charcoal In ethanol; water at 80℃; for 1h;

: 1197396-47-6
(3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: (3R,4R,5S)-ethyl-4-(N-acetylacetamide)-5-(1,3-dioxoisoindolin-2-yl)-3-(3-pentyloxy)cyclohex-1-ene carboxylate With hydrazine hydrate In ethanol at 50℃; for 14h; Inert atmosphere; Stage #2: With hydrogenchloride; water In ethanol Stage #3: With ammonium hydroxide In water pH=11;	96%

: C21H36N2O6

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With trifluoroacetic acid In isopropyl alcohol at 0 - 30℃; for 7h; Solvent; Reagent/catalyst; Temperature;	96%

: 204255-06-1
oseltamivir

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With hydrogen at 20℃; under 380.026 Torr; for 3h;	98.5%
With tributylphosphine; acetic acid In ethanol; water at 5 - 25℃; for 5.5 - 9h;	97%
With triphenylphosphine In tetrahydrofuran; water at 50℃; for 10h;	96%

: (1S,2R,3S,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)-2-(p-tolylthio)cyclohexanecarboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With potassium carbonate In ethanol at 23℃; for 4h; retro Michael reaction;	91%
With potassium carbonate In ethanol at 23℃; for 4h; Product distribution / selectivity;	91%
Stage #1: (1S,2R,3S,4R,5S)-ethyl 4-acetamido-5-amino-3-(pentan-3-yloxy)-2-(p-tolylthio)cyclohexanecarboxylate With ammonia In ethanol at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With potassium carbonate In ethanol at 23℃; for 6h; Inert atmosphere;	45.2 mg

: 204255-11-8
oseltamivir phosphate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With sodium hydrogencarbonate In water at 20℃; for 0.0833333h; Inert atmosphere;	98%
Stage #1: oseltamivir phosphate In dichloromethane; water at 25 - 30℃; for 0.166667h; Stage #2: With ammonia In dichloromethane; water pH=9 - 10; Stage #3: In n-heptane at 25 - 30℃; for 1h; Purification / work up;
Stage #1: oseltamivir phosphate In dichloromethane; water at 25 - 30℃; for 0.166667h; Stage #2: With ammonia In dichloromethane; water pH=9 - 10; Stage #3: In n-heptane; toluene at 20 - 30℃; for 3.5h; Purification / work up;
In dichloromethane; water at 20℃; for 0.75h;

: 651324-07-1
ethyl (3R,4R,5S)-4-N-acetyl(1,1-dimethylethyl)amino-5-N,N-diallylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: hydrogenchloride / water; ethanol / 13 - 25 °C 2: trifluoroacetic acid / 1.5 h / 50 °C 3: 1,3-dimethylbarbituric acid; triphenylphosphine; palladium diacetate / ethanol / 2 h / 35 °C / Sealed tube; Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: trifluoroacetic acid / dichloromethane / 1 h / 50 °C 2: 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine / ethanol / 2 h / 20 - 25 °C / Inert atmosphere View Scheme
Multi-step reaction with 2 steps 1: 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine / ethanol / 2 h / 20 - 25 °C / Inert atmosphere 2: trifluoroacetic acid / dichloromethane / 2 h / 35 - 40 °C View Scheme
With 1,3-dimethylbarbituric acid; palladium diacetate; triphenylphosphine In ethanol; water at 50℃;

: C20H36N2O4

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With trifluoroacetic acid In dichloromethane at 35 - 40℃; for 2h;
With trifluoroacetic acid In dichloromethane at 50℃; for 2h; Reagent/catalyst; Solvent;

: 891831-22-4
tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: tert-butyl [(1S,5R,6R)-6-acetylamino-3-cyano-5-(1-ethylpropoxy)cyclohex-3-en-1-yl]carbamate With hydrogenchloride In ethanol at 60℃; for 4h; Stage #2: With water In ethanol at 4℃; for 3h;	53%

: (3R,4R)-ethyl 4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

A: 1402431-91-7
ethyl (3R,4R,5R)-4-acetylamino-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

B: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With chloro-trimethyl-silane; ethanol; zinc In tetrahydrofuran; toluene at 70℃; for 2h; Flow reactor;	A n/a B n/a

: 1362750-80-8
C19H35N2O4P

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: C19H35N2O4P With hydrogenchloride; water In dichloromethane; toluene at 20℃; for 4h; Stage #2: With sodium hydrogencarbonate In dichloromethane; water; toluene pH=10;	53.2 mg

: 1443055-49-9
(3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: (3R,4R,5S)-ethyl 4-acetylamino-3-(pentan-3-yloxy)-5-(2,2,2-trichloroacetamido)cyclohex-1-enecarboxylate With caesium carbonate In dimethyl sulfoxide at 80℃; for 0.25h; Stage #2: With acetic acid In water; dimethyl sulfoxide at 80℃; for 0.333333h;

: 949164-64-1
ethyl (3R,4R,5S)-4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With acetic acid; zinc at 20℃; for 34h; Inert atmosphere;	81%
Stage #1: ethyl (3R,4R,5S)-4-acetamido-5-nitro-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate With acetic acid; zinc In ethanol at 70℃; Inert atmosphere; Reflux; Stage #2: With ammonium hydroxide In ethanol; water at 20℃; pH=8; Inert atmosphere;	71%
With hydrogenchloride In water at 50℃; for 1h; Inert atmosphere;
With chloro-trimethyl-silane; acetic acid; zinc In diethyl ether for 8h; Reflux;

: 927395-63-9
(3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene

: 64-17-5
ethanol

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Stage #1: (3R,4R,5S)-4-acetylamino-5-benzyloxycarbonylamino-1-cyano-3-(1-ethylpropoxy)cyclohexene; ethanol With hydrogenchloride at 20℃; for 24h; Stage #2: With water In ethanol at 20℃; for 2h; Stage #3: With ammonium hydroxide In ethanol at 20℃; for 10h;	74%

: 1196490-17-1
ethyl (3R,4R,5R,6R)-4-acetamido-5-azido-6-(methylsulfonyloxy)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

A: 1196490-21-7
C16H27NO4

B: 1052063-39-4
ethyl (3S,4R,5R)-4-acetamido-3-amino-5-(pentan-3-yloxy)-cyclohex-1-enecarboxylate

C: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With sodium tetrahydroborate In tetrahydrofuran; ethanol at -30 - 20℃;

...Expand

: 204254-96-6
(1S,5R,6S)-5-(pentan-3-yloxy)-7-oxabicyclo[4.1.0]hept-3-ene-3-carboxylic acid ethyl ester

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 7 steps 1.1: 97 percent / MgBr2*OEt2 / acetonitrile; various solvent(s) / 16 h / 55 °C 2.1: ethanolamine; Pd/C / ethanol / 3 h / Heating 2.2: 77 percent / H2SO4 3.1: various solvent(s) 4.1: Et3N / various solvent(s) 5.1: various solvent(s) / 15 h / 111 - 112 °C / 2625.21 - 3375.27 Torr 6.1: AcOH; MeSO3H / various solvent(s) / 15 h / 20 °C 7.1: NH2CH2CH2OH; Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 7 steps 1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating 1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating 2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr 3.1: Et3N / ethyl acetate / 0 - 20 °C 4.1: MeSO3H / ethanol / 2.67 h / Heating 5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr 6.1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 7.1: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 7 steps 1.1: MgBr2*OEt2 / acetonitrile; various solvent(s) / Heating 1.2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating 2.1: 6 h / 100 °C / 750.08 - 3750.38 Torr 3.1: Et3N / ethyl acetate / 0 - 20 °C 4.1: MeSO3H / ethanol / 2.67 h / Heating 5.1: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr 6.1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 7.1: HOCH2CH2OH / Pd/C / ethanol / Heating View Scheme

: 312904-12-4
ethyl (3R,4S,5R)-5-amino-3-(1-ethylpropoxy)-4-hydroxy-1-cyclohexene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 5 steps 1: various solvent(s) 2: Et3N / various solvent(s) 3: various solvent(s) / 15 h / 111 - 112 °C / 2625.21 - 3375.27 Torr 4: AcOH; MeSO3H / various solvent(s) / 15 h / 20 °C 5: NH2CH2CH2OH; Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 6 h / 100 °C / 750.08 - 3750.38 Torr 2: Et3N / ethyl acetate / 0 - 20 °C 3: MeSO3H / ethanol / 2.67 h / Heating 4: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr 5: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 6: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 6 steps 1: 6 h / 100 °C / 750.08 - 3750.38 Torr 2: Et3N / ethyl acetate / 0 - 20 °C 3: MeSO3H / ethanol / 2.67 h / Heating 4: ethyl acetate / 6 h / 112 °C / 750.08 - 4500.45 Torr 5: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 6: HOCH2CH2OH / Pd/C / ethanol / Heating View Scheme
Multi-step reaction with 6 steps 1: acetonitrile / 1 h / 35 °C 2: pyridine / chloroform / 3 h / -5 °C 3: pyridine / tert-butyl methyl ether / 10 h / 80 °C 4: hydrogen; palladium on activated charcoal / ethanol / 8 h / 35 °C / 760.05 Torr 5: tert-butyl methyl ether / 2 h / 40 °C 6: trifluoroacetic acid / isopropyl alcohol / 7 h / 0 - 30 °C View Scheme

: 584-02-1
2-pentanol

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 3 steps 1: BF3*Et2O / 2 h / 70 - 75 °C 2: pyridine, (dimethylamino)pyridine / 18 h / Ambient temperature 3: Ph3P, H2O / tetrahydrofuran / 10 h / 50 °C View Scheme
Multi-step reaction with 4 steps 1: boron trifluoride diethyl etherate / 75 °C / Inert atmosphere 2: pyridine; dmap / 1 h / 150 °C / Inert atmosphere; Microwave irradiation 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: hydrazine / ethanol / 10 h / 68 °C / Inert atmosphere View Scheme
Multi-step reaction with 4 steps 1: boron trifluoride diethyl etherate / 75 °C / Inert atmosphere 2: pyridine; dmap / 1 h / 150 °C / Inert atmosphere; Microwave irradiation 3: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.5 h / 20 °C / Inert atmosphere 4: hydrazine / ethanol / 10 h / 68 °C / Inert atmosphere View Scheme

: 1158724-89-0
C24H34N2O6

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
With hydrogenchloride In 1,4-dioxane; ethanol at 20℃; for 24h;	83%

: 1141364-90-0
2-(1-ethylpropoxy)acetaldehyde

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 9 steps 1.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; chloroacetic acid / toluene 2.1: caesium carbonate / 4 h / 0 - 20 °C 3.1: -15 °C 4.1: trifluoroacetic acid / toluene / 4 h / 20 °C 5.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0.33 h / 20 °C 6.1: trimethylsilylazide / toluene / 0.33 h / 20 °C 7.1: acetic acid / 48 h / 20 °C 8.1: chloro-trimethyl-silane; zinc / ethanol / 70 °C 8.2: 0 °C 9.1: potassium carbonate / 20 °C View Scheme
Multi-step reaction with 5 steps 1.1: (R)-2-(diphenyl(trimethylsilyloxy)methyl)pyrrolidine; chloroacetic acid / toluene / 6 h / 23 °C / Inert atmosphere 1.2: 2 h / 23 °C / Inert atmosphere 2.1: trifluoroacetic acid / toluene / 4 h / 23 °C / Inert atmosphere 3.1: oxalyl dichloride; N,N-dimethyl-formamide / toluene / 0.5 h / 23 °C / Inert atmosphere 4.1: pyridine; trimethylsilylazide / N,N-dimethyl-formamide / 20 °C / Microflow reaction; Inert atmosphere 4.2: 110 °C / Microflow reaction; Inert atmosphere 5.1: chloro-trimethyl-silane; zinc / ethanol / 2 h / 70 °C / Inert atmosphere 5.2: 0.17 h / 0 °C / Inert atmosphere 5.3: 9 h / 23 °C / Inert atmosphere View Scheme
Multi-step reaction with 3 steps 1: (2S)-2-{diphenyl[(trimethylsilyl)oxy]methyl}pyrrolidine; chloroacetic acid / dimethyl sulfoxide / 20 °C 2: 1,8-diazabicyclo[5.4.0]undec-7-ene; lithium chloride / acetonitrile / 70 °C / Inert atmosphere 3: acetic acid; zinc / 34 h / 20 °C / Inert atmosphere View Scheme

: 1226768-14-4
N-((2R,3S)-1-nitro-4-oxo-3-(pentan-3-yloxy)butan-2-yl)acetamide

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 4 steps 1: caesium carbonate / 3 h / 0 °C 2: 36 h / -15 °C 3: chloro-trimethyl-silane; zinc / 2 h / -15 - 70 °C 4: ammonia; potassium carbonate / 14 h / 20 °C View Scheme
Multi-step reaction with 4 steps 1.1: caesium carbonate / 3 h / 0 °C 1.2: 1 h 2.1: 36 h / -15 °C 3.1: chloro-trimethyl-silane; zinc / 2 h / -15 - 70 °C 4.1: ammonia; potassium carbonate / 14 h / 20 °C View Scheme
Multi-step reaction with 5 steps 1: potassium carbonate / acetonitrile / 3 h / 0 - 20 °C 2: zinc; acetic acid / ethanol / 0.5 h / 70 °C / Inert atmosphere 3: acetonitrile / 4 h / 20 °C 4: lithium chloride / dimethyl sulfoxide / 2 h / 190 °C / Inert atmosphere 5: trifluoroacetic acid / dichloromethane / 4 h / 20 °C / Inert atmosphere View Scheme

: 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

: 196618-13-0
oseltamivir

Conditions

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 20℃; for 24h; Stage #2: With water at 4 - 20℃; for 7.5h;	60%

: 312904-15-7
ethyl (3R,4R,5S)-5-N-allylamino-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: AcOH; MeSO3H / various solvent(s) / 15 h / 20 °C 2: NH2CH2CH2OH; Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 2: H2NCH2CH2OH / Pd/C / ethanol / 3 h / Heating View Scheme
Multi-step reaction with 2 steps 1: AcOH; MeSO3H / various solvent(s) / 0 - 20 °C 2: HOCH2CH2OH / Pd/C / ethanol / Heating View Scheme

: argon

: 144-55-8
sodium hydrogencarbonate

: 107-11-9
1-amino-2-propene

A: 196618-13-0
oseltamivir

B: 312904-15-7
ethyl (3R,4R,5S)-5-N-allylamino-4-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions

Conditions	Yield
With sodium sulfate In ethyl acetate

...Expand

: 1132659-99-4
(3R,4S,5R)-4-acetylamino-3-(1-ethyl-propoxy)-5-methanesulfonyloxy-cyclohex-1-enecarboxylic acid ethyl ester

: 196618-13-0
oseltamivir

Conditions

Conditions	Yield
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 8 h / 90 °C 2: water; triphenylphosphine / tetrahydrofuran / 8 h / Reflux View Scheme
Multi-step reaction with 2 steps 1: sodium azide / N,N-dimethyl-formamide / 3 h / 80 °C 2: hydrogen / ethanol / 20 °C View Scheme
Multi-step reaction with 2 steps 1.1: sodium azide / ethanol; water / 8 h / Reflux 2.1: triphenylphosphine / tetrahydrofuran / 4 h / 20 °C 2.2: Staudinger Azide Reduction / 24 h / 20 °C View Scheme

: 207857-15-6
1,3-di(tert-butyloxycarbonyl)-2-(trifluoromethylsulfonyl)guanidine

: 196618-13-0
oseltamivir

: 208720-81-4
(3R,4R,5S)-5-[[(1Z)-[[(tert-butoxy)carbonyl]amino]([[(tert-butoxy)carbonyl]imino])methyl]amino]-4-acetylamino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With triethylamine In dichloromethane	100%

: 196618-13-0
oseltamivir

: oseltamivir acid

Conditions

Conditions	Yield
With sodium hydroxide In ethanol at 90℃; for 2h;	99%
Stage #1: oseltamivir With potassium hydroxide; water In tetrahydrofuran at 0 - 20℃; for 1h; Stage #2: With Amberlite IR-120 In tetrahydrofuran pH=5;	88%
Stage #1: oseltamivir With potassium hydroxide In methanol; water Stage #2: In methanol; water for 0.0833333h;	79%

: 196618-13-0
oseltamivir

: 204255-06-1
oseltamivir

Conditions

Conditions	Yield
With fluorosulfonyl azide; potassium hydrogencarbonate In tert-butyl methyl ether; water; N,N-dimethyl-formamide at 20℃; for 0.5h;	99%

: 196618-13-0
oseltamivir

: 204255-11-8
oseltamivir phosphate

Conditions

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%

: 75-89-8
2,2,2-trifluoroethanol

: 196618-13-0
oseltamivir

: (3R,4R,5S)-4-acetylamino-5-trifluoroacetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With copper(l) iodide; 9-azabicyclo<3.3.1>nonane-N-oxyl; oxygen; 4,4'-di-tert-butyl-2,2'-bipyridine In acetonitrile at 20℃; under 760.051 Torr; for 4h; Sealed tube;	90%

: 145013-05-4
tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanethioyl)carbamate

: 196618-13-0
oseltamivir

: ethyl (3R,4R,5S)-4-acetamido-5-[N2,N3-bis(tert-butoxycarbonyl)guanidino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate

Conditions

Conditions	Yield
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 0℃;	89%
With triethylamine In N,N-dimethyl-formamide at 0 - 20℃;	89%
With triethylamine; mercury dichloride In N,N-dimethyl-formamide at 20℃; for 10h;	177 mg

: 86119-84-8, 7664-38-2
phosphoric acid

: 196618-13-0
oseltamivir

: 204255-11-8
oseltamivir phosphate

Conditions

Conditions	Yield
In ethanol; water at 50 - 55℃; for 1.5 - 2h;	88%

: 19350-66-4
2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylic acid 3,5-diethyl ester

: 196618-13-0
oseltamivir

: diethyl 4-(((1S,5R,6R)-6-acetamido-3-(ethoxycarbonyl)-5-(pentan-3-yloxy)cyclohex-3-en-1-yl)carbamoyl)-2,6-dimethyl-1,4-dihydropyridine-3,5-dicarboxylate

Conditions

Conditions	Yield
Stage #1: 2,6-dimethyl-1,4-dihydropyridine-3,4,5-tricarboxylic acid 3,5-diethyl ester With triethylamine; isobutyl chloroformate In dichloromethane at 0 - 20℃; for 0.5h; Inert atmosphere; Stage #2: oseltamivir In dichloromethane at 20℃; Inert atmosphere;	87%

: 34619-03-9
tert-butyldicarbonate

: 196618-13-0
oseltamivir

: 367252-68-4
(3R,4R,5S)-ethyl 4-acetamido-5-((tert-butoxycarbonyl)amino)-3-(pentan-3-yloxy)cyclohex-1-enecarboxylate

Conditions

Conditions	Yield
With triethylamine In methanol at 0 - 20℃; for 18h;	86%
With triethylamine In methanol at 0 - 20℃; for 18h;	86%

: 67443-38-3
5-bromo-2-chloro-3-nitropyridine

: 196618-13-0
oseltamivir

: (3R,4R,5S)-4-acetamido-5-[2-(5-bromo-3-nitro)pyridinylamino]-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With potassium carbonate In N,N-dimethyl-formamide at 60℃;	82%

: 196618-13-0
oseltamivir

: C16H28N2O4*H3O4P

Conditions

Conditions	Yield
With phosphoric acid In ethanol; water at 65 - 75℃; for 8h; pH=4; Temperature; pH-value;	81.9%

: 124-63-0
methanesulfonyl chloride

: 196618-13-0
oseltamivir

: C17H30N2O6S

Conditions

Conditions	Yield
With triethylamine In dichloromethane at 20℃; for 2h;	80%
With triethylamine In dichloromethane at 0℃;

: hexyloxycarbonyl isothiocyanate

: 196618-13-0
oseltamivir

: (3R,4R,5S)-4-acetamido-5-[N-(N′-n-hexyloxycarbonyl)thioureido]-3-(1-ethylpropoxy)-cyclohex-1-en-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
In dichloromethane at 20℃; for 2h;	75%

: 64-19-7
acetic acid

: 196618-13-0
oseltamivir

: 1191921-01-3
(3R,4R,5S)-4-acetylamino-5-acetylamino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylic acid ethyl ester

Conditions

Conditions	Yield
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate at 20℃;	74.5%
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃;

Oseltamivir Specification

The 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- , with cas register number of 196618-13-0, belongs to the classification codes of (1)anti-infective agents ; (2)antiviral agents ; (3)enzyme inhibitors ; (4)influenza treatment. It also has other names such as Oseltamivir ; Ethyl (3R,4R,5S)-4-acetamido-5-amino-3-(1-ethylpropoxy)-1-cyclohexene-1-carboxylate . Its IUPAC name is ethyl (3R,4R,5S)-4-acetamido-5-amino-3-pentan-3-yloxycyclohexene-1-carboxylate . And its systematic name is also called ethyl (3R,4R,5S)-4-(acetylamino)-5-amino-3-(pentan-3-yloxy)cyclohex-1-ene-1-carboxylate .

Physical properties of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- are: (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) Index of Refraction: 1.502 ; (13) Molar Refractivity: 84.66 cm³ ; (14) Molar Volume: 286.7 cm³ ; (15) Surface Tension: 41.1 dyne/cm ; (16) Density: 1.08 g/cm³ ; (17) Flash Point: 240 °C ; (18) Enthalpy of Vaporization: 73.64 kJ/mol ; (19) Boiling Point: 473.3 °C at 760 mmHg ; (20) Vapour Pressure: 3.98E-09 mmHg at 25°C.

Uses of 1-Cyclohexene-1-carboxylicacid, 4-(acetylamino)-5-amino-3-(1-ethylpropoxy)-, ethyl ester, (3R,4R,5S)- : This compound is an acetamido cyclohexene that is a structural homolog of SIALIC ACID and inhibits neuraminidase. It has been used as a drug for treatment of influenza.

You can still convert the following datas into molecular structure:
(1) SMILES:O=C(OCC)/C1=C/[C@@H](OC(CC)CC)[C@H](NC(=O)C)[C@@H](N)C1;
(2) InChI:InChI=1/C16H28N2O4/c1-5-12(6-2)22-14-9-11(16(20)21-7-3)8-13(17)15(14)18-10(4)19/h9,12-15H,5-8,17H2,1-4H3,(H,18,19)/t13-,14+,15+/m0/s1;
(3) InChIKey:VSZGPKBBMSAYNT-RRFJBIMHBB

Product Name

Oseltamivir

Synthetic route

Oseltamivir Specification

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